Scientific production
2019 |
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| 128. | G. Zong; Z. Hu; S. O’Keefe; D. Tranter; M. J Iannotti; L. Baron; B. Hall; K. Corfield; A. O Paatero; M. J Henderson; P. Roboti; J. Zhou; X. Sun; M. Govindarajan; J. M Rohde; N. Blanchard; R. Simmonds; J. Inglese; Y. Du; C. Demangel; S. High; V. O Paavilainen; W. Q Shi Ipomoeassin F Binds Sec61α to Inhibit Protein Translocation Journal Article Journal of the American Chemical Society 2019, 141, 8450-8461. @article{doi:10.1021/jacs.8b13506, title = {Ipomoeassin F Binds Sec61α to Inhibit Protein Translocation}, author = {G. Zong and Z. Hu and S. O’Keefe and D. Tranter and M. J Iannotti and L. Baron and B. Hall and K. Corfield and A. O Paatero and M. J Henderson and P. Roboti and J. Zhou and X. Sun and M. Govindarajan and J. M Rohde and N. Blanchard and R. Simmonds and J. Inglese and Y. Du and C. Demangel and S. High and V. O Paavilainen and W. Q Shi}, url = {https://doi.org/10.1021/jacs.8b13506}, doi = {10.1021/jacs.8b13506}, year = {2019}, date = {2019-06-01}, journal = {Journal of the American Chemical Society}, volume = {141}, number = {21}, pages = {8450-8461}, note = {PMID: 31059257}, keywords = {BSM}, pubstate = {published}, tppubtype = {article} } |
| 127. | M. Pichon; F. Stauffert; A. Bodlenner; P. Compain Tight-binding Inhibition of Jack bean alpha-Mannosidase by Glycoimidazole Clusters Journal Article Organic & biomolecular chemistry 2019, 17, 5801-5817 . @article{pichon2019tight, title = {Tight-binding Inhibition of Jack bean alpha-Mannosidase by Glycoimidazole Clusters}, author = {M. Pichon and F. Stauffert and A. Bodlenner and P. Compain}, url = {https://pubs.rsc.org/en/content/articlelanding/2019/ob/c9ob00826h#!divAbstract}, doi = {10.1039/C9OB00826H}, year = {2019}, date = {2019-05-21}, journal = {Organic & biomolecular chemistry}, volume = {17}, pages = {5801-5817 }, publisher = {Royal Society of Chemistry}, keywords = {SYBIO}, pubstate = {published}, tppubtype = {article} } |
| 126. | C. Batisse; M. Céspedes F Dávila; M. Castello; A. Messara; B. Vivet; G. Marciniak; A. Panossian; G. Hanquet; F. R Leroux Efficient asymmetric synthesis of aryl difluoromethyl sulfoxides and their use to access enantiopure α-difluoromethyl alcohols Journal Article Tetrahedron 2019, 75, 3063 - 3079. @article{BATISSE20193063, title = {Efficient asymmetric synthesis of aryl difluoromethyl sulfoxides and their use to access enantiopure α-difluoromethyl alcohols}, author = {C. Batisse and M. Céspedes F Dávila and M. Castello and A. Messara and B. Vivet and G. Marciniak and A. Panossian and G. Hanquet and F. R Leroux}, url = {http://www.sciencedirect.com/science/article/pii/S0040402019304491}, doi = {https://doi.org/10.1016/j.tet.2019.04.037}, issn = {0040-4020}, year = {2019}, date = {2019-05-15}, journal = {Tetrahedron}, volume = {75}, number = {23}, pages = {3063 - 3079}, abstract = {The -CHF2 moiety has shown a growing interest in pharmaceutical and agrochemical applications over the last few years. Its introduction is therefore a current research topic for organic chemists. Several groups have reported the synthesis of difluoromethylated compounds. However, the more challenging enantioselective introduction of the difluoromethyl group has been scarcely described yet. We recently developed a new strategy, based on the use of an enantiopure difluoromethyl sulfoxide used as chiral and traceless auxiliary, for the synthesis of highly enantioenriched α-difluoromethyl alcohols. The first method developed in our laboratory aims to access highly stereoenriched α,α-difluoro-β-hydroxysulfoxides through the condensation of the enantiopure difluoromethyl sulfoxide on carbonyl derivatives. It is noteworthy that highly diastereo- and enantioenriched α,α-difluoro-β-hydroxysulfoxides can also be accessed after the diastereoselective reduction of highly enantioenriched α,α-difluoro-β-ketosulfoxides. Finally, the expected difluoromethyl-substituted alcohols can be obtained after removal of the chiral auxiliary with complete retention of stereoenrichment at carbon.}, keywords = {COHA}, pubstate = {published}, tppubtype = {article} } The -CHF2 moiety has shown a growing interest in pharmaceutical and agrochemical applications over the last few years. Its introduction is therefore a current research topic for organic chemists. Several groups have reported the synthesis of difluoromethylated compounds. However, the more challenging enantioselective introduction of the difluoromethyl group has been scarcely described yet. We recently developed a new strategy, based on the use of an enantiopure difluoromethyl sulfoxide used as chiral and traceless auxiliary, for the synthesis of highly enantioenriched α-difluoromethyl alcohols. The first method developed in our laboratory aims to access highly stereoenriched α,α-difluoro-β-hydroxysulfoxides through the condensation of the enantiopure difluoromethyl sulfoxide on carbonyl derivatives. It is noteworthy that highly diastereo- and enantioenriched α,α-difluoro-β-hydroxysulfoxides can also be accessed after the diastereoselective reduction of highly enantioenriched α,α-difluoro-β-ketosulfoxides. Finally, the expected difluoromethyl-substituted alcohols can be obtained after removal of the chiral auxiliary with complete retention of stereoenrichment at carbon. |
| 125. | V. Bizet; N. Blanchard Acid Fluorides in Transition-Metal Catalysis: A Good Balance between Stability and Reactivity Journal Article Angewandte Chemie International Edition 2019, 58, 6814-6817. @article{bizet:hal-02107607, title = {Acid Fluorides in Transition-Metal Catalysis: A Good Balance between Stability and Reactivity}, author = {V. Bizet and N. Blanchard}, url = {https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201900591}, doi = {10.1002/anie.201900591}, year = {2019}, date = {2019-04-25}, journal = {Angewandte Chemie International Edition}, volume = {58}, pages = {6814-6817}, publisher = {Wiley-VCH Verlag}, keywords = {BSM}, pubstate = {published}, tppubtype = {article} } |
| 124. | L. Naranjo; F. Ferrara; N. Blanchard; C. Demangel; S. D’Angelo; M. F. Erasmus; A. A. Teixeira; and A. R.M. Bradbury Recombinant Antibodies against Mycolactone Journal Article Toxins 2019, 11, 346. @article{, title = {Recombinant Antibodies against Mycolactone}, author = {L. Naranjo and F. Ferrara and N. Blanchard and C. Demangel and S. D’Angelo and M. F. Erasmus and A. A. Teixeira and and A. R.M. Bradbury}, url = {https://www.mdpi.com/2072-6651/11/6/346}, doi = {10.3390/toxins11060346}, year = {2019}, date = {2019-04-10}, journal = {Toxins}, volume = {11}, pages = {346}, keywords = {BSM}, pubstate = {published}, tppubtype = {article} } |
| 123. | Martin-Benlloch, X.; Haid, S.; Novodomska, A.; Rominger, F.; Pietschmann, T.; Davioud-Charvet, E.; Elhabiri, M. Physicochemical Properties Govern the Activity of Potent Antiviral Flavones Journal Article ACS Omega 2019, 4, 4871-4887. Tags: CBM @article{, title = {Physicochemical Properties Govern the Activity of Potent Antiviral Flavones}, author = {Martin-Benlloch, X. and Haid, S. and Novodomska, A. and Rominger, F. and Pietschmann, T. and Davioud-Charvet, E. and Elhabiri, M.}, year = {2019}, date = {2019-03-31}, journal = {ACS Omega}, volume = {4}, pages = {4871-4887}, keywords = {CBM}, pubstate = {published}, tppubtype = {article} } |
| 122. | M. Holler; B. Delavaux-Nicot; J.-F. Nierengarten Topological and Steric Constraints to Stabilize Heteroleptic Copper(I) Complexes Combining Phenanthroline Ligands and Phosphines Journal Article Chemistry – A European Journal 2019, 25, 4543-4550. @article{doi:10.1002/chem.201805671b, title = {Topological and Steric Constraints to Stabilize Heteroleptic Copper(I) Complexes Combining Phenanthroline Ligands and Phosphines}, author = {M. Holler and B. Delavaux-Nicot and J.-F. Nierengarten}, url = {https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201805671}, doi = {10.1002/chem.201805671}, year = {2019}, date = {2019-03-27}, journal = {Chemistry – A European Journal}, volume = {25}, number = {18}, pages = {4543-4550}, abstract = {Abstract Heteroleptic copper(I) complexes combining phenanthroline derivatives (NN) and chelating bisphosphine ligands (PP) are an important class of luminescent materials for various applications. Although thermodynamically stable, [Cu(NN)(PP)]+ derivatives are also kinetically unstable. As a result, a dynamic ligand-exchange reaction is often observed in solution, leading to a dynamic mixture of heteroleptic and homoleptic complexes. To prevent the formation of the homoleptic species, macrocyclic phenanthroline ligands have been used for the preparation of [Cu(NN)(PP)]+ pseudorotaxanes. The topological constraint resulting from the macrocyclic structure of the NN ligand drives the thermodynamic equilibrium towards the exclusive formation of the heteroleptic complex as long as the macrocycle is large and flexible enough to allow for the threading of the PP ligand. Conversely, when the threading is prevented by steric constraints, unprecedented copper(I) complexes with a trigonal coordination geometry are obtained. These results are summarized in the present concept article.}, keywords = {CMM}, pubstate = {published}, tppubtype = {article} } Abstract Heteroleptic copper(I) complexes combining phenanthroline derivatives (NN) and chelating bisphosphine ligands (PP) are an important class of luminescent materials for various applications. Although thermodynamically stable, [Cu(NN)(PP)]+ derivatives are also kinetically unstable. As a result, a dynamic ligand-exchange reaction is often observed in solution, leading to a dynamic mixture of heteroleptic and homoleptic complexes. To prevent the formation of the homoleptic species, macrocyclic phenanthroline ligands have been used for the preparation of [Cu(NN)(PP)]+ pseudorotaxanes. The topological constraint resulting from the macrocyclic structure of the NN ligand drives the thermodynamic equilibrium towards the exclusive formation of the heteroleptic complex as long as the macrocycle is large and flexible enough to allow for the threading of the PP ligand. Conversely, when the threading is prevented by steric constraints, unprecedented copper(I) complexes with a trigonal coordination geometry are obtained. These results are summarized in the present concept article. |
| 121. | L. Lefebvre; J. Kelber; X. Mao; F. Ponzio; G. Agusti; C. Vigier-Carrière; V.; L. Jierry; V. Ritleng; D. Edouard Environmental Progress & Sustainable Energy 2019, 38, 329-335. @article{doi:10.1002/ep.12944, title = {Borohydride-functionalized polydopamine-coated open cell polyurethane foam as a reusable soft structured material for reduction reactions: Application to the removal of a dye}, author = {L. Lefebvre and J. Kelber and X. Mao and F. Ponzio and G. Agusti and C. Vigier-Carrière and V. and L. Jierry and V. Ritleng and D. Edouard}, url = {https://onlinelibrary.wiley.com/doi/abs/10.1002/ep.12944}, doi = {10.1002/ep.12944}, year = {2019}, date = {2019-03-22}, journal = {Environmental Progress & Sustainable Energy}, volume = {38}, number = {2}, pages = {329-335}, abstract = {Open cell polyurethane foams coated with mussel-inspired polydopamine can be used as support for borohydride anions through their complexation by the catechol groups of the polydopamine layer. This strong interaction prevents borohydride hydrolysis and oxidation, and based on the redox mediator properties of polydopamine, the so-functionalized polydopamine-coated open cell polyurethane foams can act as efficient and reusable soft structured materials for the reduction of methylene blue in aqueous solution without additional sodium borohydride (NaBH4). Very low amounts of released boron sub-products and very small potential of hydrogen (pH) increase are observed in comparison to previous processes using dissolved NaBH4. This considerably reduces the environmental impact of the reducing structured material on the treated wastewater compared to the latter. © 2018 American Institute of Chemical Engineers Environ Prog, 38: 329–335, 2019}, keywords = {COA}, pubstate = {published}, tppubtype = {article} } Open cell polyurethane foams coated with mussel-inspired polydopamine can be used as support for borohydride anions through their complexation by the catechol groups of the polydopamine layer. This strong interaction prevents borohydride hydrolysis and oxidation, and based on the redox mediator properties of polydopamine, the so-functionalized polydopamine-coated open cell polyurethane foams can act as efficient and reusable soft structured materials for the reduction of methylene blue in aqueous solution without additional sodium borohydride (NaBH4). Very low amounts of released boron sub-products and very small potential of hydrogen (pH) increase are observed in comparison to previous processes using dissolved NaBH4. This considerably reduces the environmental impact of the reducing structured material on the treated wastewater compared to the latter. © 2018 American Institute of Chemical Engineers Environ Prog, 38: 329–335, 2019 |
| 120. | T. Saied; C. Demangeat; A. Panossian; F. R. Leroux; Y. Fort; C. Comoy Transition‐Metal‐Free Heterobiaryl Synthesis via Aryne Coupling Journal Article European Journal of Organic Chemistry 2019, early view,. @article{, title = {Transition‐Metal‐Free Heterobiaryl Synthesis via Aryne Coupling}, author = {T. Saied and C. Demangeat and A. Panossian and F. R. Leroux and Y. Fort and C. Comoy}, url = {https://onlinelibrary.wiley.com/doi/10.1002/ejoc.201900130}, doi = {10.1002/ejoc.201900130}, year = {2019}, date = {2019-03-06}, journal = {European Journal of Organic Chemistry}, volume = {early view}, keywords = {COHA}, pubstate = {published}, tppubtype = {article} } |
| 119. | S Jerhaoui; J-P Djukic; J Wencel-Delord; F Colobert Asymmetric, Nearly Barrierless C(sp3)–H Activation Promoted by Easily-Accessible N-Protected Aminosulfoxides as New Chiral Ligands Journal Article ACS Catalysis 2019, 9, 2532-2542. @article{doi:10.1021/acscatal.8b04946, title = {Asymmetric, Nearly Barrierless C(sp3)–H Activation Promoted by Easily-Accessible N-Protected Aminosulfoxides as New Chiral Ligands}, author = {S Jerhaoui and J-P Djukic and J Wencel-Delord and F Colobert}, url = {https://doi.org/10.1021/acscatal.8b04946}, doi = {10.1021/acscatal.8b04946}, year = {2019}, date = {2019-03-01}, journal = {ACS Catalysis}, volume = {9}, number = {3}, pages = {2532-2542}, keywords = {SYNCAT}, pubstate = {published}, tppubtype = {article} } |
| 118. | Berroukeche, F.; Mokhtari-soulimane, N.; Imessaoudene, A.; Cherrak, A.S.; Ronot, P.; Boss, A.; Belhandouz, A.; Merzouk, H.; Elhabiri, M. Romanian Journal of Diabetes Nutrition and Metabolic Diseases 2019, 26, 39-53. @article{, title = {Oral Supplementation Effect of Iron and its Complex Form With Quercetin on Oxidant Status and on Redistribution of Essential Metals in Organs of Streptozotocin Diabetic Rats}, author = {Berroukeche, F. and Mokhtari-soulimane, N. and Imessaoudene, A. and Cherrak, A.S. and Ronot, P.; Boss, A.; Belhandouz, A. and Merzouk, H. and Elhabiri, M. }, doi = {10.2478/rjdnmd-2019-0005}, year = {2019}, date = {2019-03-01}, journal = {Romanian Journal of Diabetes Nutrition and Metabolic Diseases}, volume = {26}, pages = {39-53}, keywords = {CBM}, pubstate = {published}, tppubtype = {article} } |
| 117. | A Srinivasulu; B Shantharjun; D Vani; Chinna K Ashalu; A Mohd; J Wencel-Delord; F Colobert; R K Reddy Iron-Catalyzed Minisci Type Acetylation of N-Heteroarenes Mediated by CH(OEt)3/TBHP Journal Article European Journal of Organic Chemistry 2019, 2019, 1815-1819. Abstract | Links | Tags: SYNCAT @article{doi:10.1002/ejoc.201900033, title = {Iron-Catalyzed Minisci Type Acetylation of N-Heteroarenes Mediated by CH(OEt)3/TBHP}, author = {A Srinivasulu and B Shantharjun and D Vani and Chinna K Ashalu and A Mohd and J Wencel-Delord and F Colobert and R K Reddy}, url = {https://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.201900033}, doi = {10.1002/ejoc.201900033}, year = {2019}, date = {2019-02-28}, journal = {European Journal of Organic Chemistry}, volume = {2019}, number = {8}, pages = {1815-1819}, abstract = {Iron-catalyzed acetylation of electron deficient N-heteroarenes has been reported using triethylorthoformate as robust and inexpensive acetyl source. This new method is successfully applied for the acetylation of quinolines, isoquinoline, quinoxalines, arylpyridines, bipyridines, and benzothiazole.}, keywords = {SYNCAT}, pubstate = {published}, tppubtype = {article} } Iron-catalyzed acetylation of electron deficient N-heteroarenes has been reported using triethylorthoformate as robust and inexpensive acetyl source. This new method is successfully applied for the acetylation of quinolines, isoquinoline, quinoxalines, arylpyridines, bipyridines, and benzothiazole. |
| 116. | R. Hensienne; D. Hazelard; P. Compain Conformationally constrained fused bicyclic iminosugars: synthetic challenges and opportunities Journal Article ARKIVOC 2019, Part IV, 4-43. @article{, title = {Conformationally constrained fused bicyclic iminosugars: synthetic challenges and opportunities}, author = {R. Hensienne and D. Hazelard and P. Compain}, url = {https://www.arkat-usa.org/arkivoc-journal/browse-arkivoc/ark.5550190.p010.872}, doi = {10.24820/ark.5550190.p010.872}, year = {2019}, date = {2019-02-20}, journal = {ARKIVOC}, volume = {Part IV}, pages = {4-43}, keywords = {SYBIO}, pubstate = {published}, tppubtype = {article} } |
| 115. | C. Baudoin-Dehoux; T. Castellan; F. Rodriguez; A. Rives; F. Stauffert; V. Garcia; T. Levade; P. Compain; Y. Génisson Selective Targeting of the Interconversion between Glucosylceramide and Ceramide by Scaffold Tailoring of Iminosugar Inhibitors Journal Article Molecules 2019, 24, 354. Abstract | Links | Tags: SYBIO @article{molecules24020354, title = {Selective Targeting of the Interconversion between Glucosylceramide and Ceramide by Scaffold Tailoring of Iminosugar Inhibitors}, author = {C. Baudoin-Dehoux and T. Castellan and F. Rodriguez and A. Rives and F. Stauffert and V. Garcia and T. Levade and P. Compain and Y. Génisson}, url = {http://www.mdpi.com/1420-3049/24/2/354}, doi = {10.3390/molecules24020354}, issn = {1420-3049}, year = {2019}, date = {2019-01-20}, journal = {Molecules}, volume = {24}, number = {2}, pages = {354}, abstract = {A series of simple C-alkyl pyrrolidines already known as cytotoxic inhibitors of ceramide glucosylation in melanoma cells can be converted into their corresponding 6-membered analogues by means of a simple ring expansion. This study illustrated how an isomerisation from iminosugar pyrrolidine toward piperidine could invert their targeting from glucosylceramide (GlcCer) formation toward GlcCer hydrolysis. Thus, we found that the 5-membered ring derivatives did not inhibit the hydrolysis reaction of GlcCer catalysed by lysosomal β-glucocerebrosidase (GBA). On the other hand, the ring-expanded C-alkyl piperidine isomers, non-cytotoxic and inactive regarding ceramide glucosylation, revealed to be potent inhibitors of GBA. A molecular docking study showed that the positions of the piperidine ring of the compound 6b and its analogous 2-O-heptyl DIX 8 were similar to that of isofagomine. Furthermore, compound 6b promoted mutant GBA enhancements over 3-fold equivalent to that of the related O-Hept DIX 8 belonging to one of the most potent iminosugar-based pharmacological chaperone series reported to date.}, keywords = {SYBIO}, pubstate = {published}, tppubtype = {article} } A series of simple C-alkyl pyrrolidines already known as cytotoxic inhibitors of ceramide glucosylation in melanoma cells can be converted into their corresponding 6-membered analogues by means of a simple ring expansion. This study illustrated how an isomerisation from iminosugar pyrrolidine toward piperidine could invert their targeting from glucosylceramide (GlcCer) formation toward GlcCer hydrolysis. Thus, we found that the 5-membered ring derivatives did not inhibit the hydrolysis reaction of GlcCer catalysed by lysosomal β-glucocerebrosidase (GBA). On the other hand, the ring-expanded C-alkyl piperidine isomers, non-cytotoxic and inactive regarding ceramide glucosylation, revealed to be potent inhibitors of GBA. A molecular docking study showed that the positions of the piperidine ring of the compound 6b and its analogous 2-O-heptyl DIX 8 were similar to that of isofagomine. Furthermore, compound 6b promoted mutant GBA enhancements over 3-fold equivalent to that of the related O-Hept DIX 8 belonging to one of the most potent iminosugar-based pharmacological chaperone series reported to date. |
| 114. | S. Shahane; B. de P. Cardoso; M. J Chetcuti; V. Ritleng Benzothiazole Nickelation: An Obstacle to the Catalytic Arylation of Azoles by Cyclopentadienyl Nickel N-Heterocyclic Carbene Complexes Journal Article Catalysts 2019, 9, 76. @article{catal9010076, title = {Benzothiazole Nickelation: An Obstacle to the Catalytic Arylation of Azoles by Cyclopentadienyl Nickel N-Heterocyclic Carbene Complexes}, author = {S. Shahane and B. de P. Cardoso and M. J Chetcuti and V. Ritleng}, url = {http://www.mdpi.com/2073-4344/9/1/76}, doi = {10.3390/catal9010076}, issn = {2073-4344}, year = {2019}, date = {2019-01-14}, journal = {Catalysts}, volume = {9}, number = {1}, pages = {76}, abstract = {NiCp†L(NHC)](+) complexes (Cp† = Cp (η5-C5H5), Cp* (η5-C5Me5); NHC = N-heterocyclic carbene; L = Cl− or NCMe) have been tested as pre-catalysts for the direct arylation of benzothiazole in the presence of an alkoxide. Only the pentamethylcyclopentadienyl derivative, [NiCp*Cl(IMes)] (IMes = 1,3-bis(2,4,6-trimethylphenylimidazol-2-ylidene), enabled low conversion to the desired coupling product with phenyl iodide as the electrophilic coupling partner. In contrast, all cyclopentadienyl complexes proved to be inactive. 1H NMR studies of the “catalytic” reaction mixtures demonstrate that they cleanly convert to an unreactive C(2)-benzothiazolyl derivative, whose identity has been confirmed by an independent synthesis and characterization. The latter constitutes a potential energy well that quenches all further reactivity, and provides a rare example of C(2)-metallated azolyl complex.}, keywords = {COA}, pubstate = {published}, tppubtype = {article} } NiCp†L(NHC)](+) complexes (Cp† = Cp (η5-C5H5), Cp* (η5-C5Me5); NHC = N-heterocyclic carbene; L = Cl− or NCMe) have been tested as pre-catalysts for the direct arylation of benzothiazole in the presence of an alkoxide. Only the pentamethylcyclopentadienyl derivative, [NiCp*Cl(IMes)] (IMes = 1,3-bis(2,4,6-trimethylphenylimidazol-2-ylidene), enabled low conversion to the desired coupling product with phenyl iodide as the electrophilic coupling partner. In contrast, all cyclopentadienyl complexes proved to be inactive. 1H NMR studies of the “catalytic” reaction mixtures demonstrate that they cleanly convert to an unreactive C(2)-benzothiazolyl derivative, whose identity has been confirmed by an independent synthesis and characterization. The latter constitutes a potential energy well that quenches all further reactivity, and provides a rare example of C(2)-metallated azolyl complex. |
| 113. | L. Aloui; M. Elhabiri; C. Platas-Iglesias; D. Esteban-Gomez; R. Abidi; M. J. Chetcuti Synthesis and Characterization of Positively Charged tris-Imidazolium Calix[6]arene Hosts for Anion Recognition Journal Article ChemistrySelect 2019, 4, 321-328. @article{, title = {Synthesis and Characterization of Positively Charged tris-Imidazolium Calix[6]arene Hosts for Anion Recognition}, author = {L. Aloui and M. Elhabiri and C. Platas-Iglesias and D. Esteban-Gomez and R. Abidi and M. J. Chetcuti}, url = {https://onlinelibrary.wiley.com/doi/10.1002/slct.201803890}, year = {2019}, date = {2019-01-07}, journal = {ChemistrySelect}, volume = {4}, pages = {321-328}, keywords = {CBM, COA}, pubstate = {published}, tppubtype = {article} } |
| 112. | J.-F. Nierengarten In My Element: Copper Journal Article Chemistry – A European Journal 2019, 25, 16-18. @article{doi:10.1002/chem.201805277, title = {In My Element: Copper}, author = {J.-F. Nierengarten}, url = {https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201805277}, doi = {10.1002/chem.201805277}, year = {2019}, date = {2019-01-02}, journal = {Chemistry – A European Journal}, volume = {25}, number = {1}, pages = {16-18}, abstract = {The In My Element series celebrates the personal accounts from Chemistry – A European Journal Editorial Board members for the 2019 International Year of the Periodic Table. In this contribution, Jean-François Nierengarten gives his story on copper.}, keywords = {CMM}, pubstate = {published}, tppubtype = {article} } The In My Element series celebrates the personal accounts from Chemistry – A European Journal Editorial Board members for the 2019 International Year of the Periodic Table. In this contribution, Jean-François Nierengarten gives his story on copper. |
| 111. | K. Tait; S. Koh; N. Blanchard; W. Tam Ruthenium-catalyzed ring-opening reaction of a 3-aza-2-oxabicyclo[2.2.1]hept-5-ene with amines - an unexpected mode of ring-opening Journal Article Canadian Journal of Chemistry 2019, 97, 310-316. @article{tait:hal-02107602, title = {Ruthenium-catalyzed ring-opening reaction of a 3-aza-2-oxabicyclo[2.2.1]hept-5-ene with amines - an unexpected mode of ring-opening}, author = {K. Tait and S. Koh and N. Blanchard and W. Tam}, url = {https://hal.archives-ouvertes.fr/hal-02107602}, doi = {10.1139/cjc-2018-0444}, year = {2019}, date = {2019-01-01}, journal = {Canadian Journal of Chemistry}, volume = {97}, number = {4}, pages = {310-316}, publisher = {NRC Research Press}, keywords = {BSM}, pubstate = {published}, tppubtype = {article} } |
| 110. | A. Songy; J. Vallet; M. Gantet; A. Boos; P. Ronot; C. Tarnus; C. Clément; P. Larignon; M.-L. Goddard; F. Fontaine Sodium arsenite effect on Vitis vinifera L. Physiology Journal Article Journal of Plant Physiology 2019, 238, 72 - 79. @article{SONGY201972, title = {Sodium arsenite effect on Vitis vinifera L. Physiology}, author = {A. Songy and J. Vallet and M. Gantet and A. Boos and P. Ronot and C. Tarnus and C. Clément and P. Larignon and M.-L. Goddard and F. Fontaine}, url = {http://www.sciencedirect.com/science/article/pii/S0176161719300732}, doi = {https://doi.org/10.1016/j.jplph.2019.05.010}, issn = {0176-1617}, year = {2019}, date = {2019-01-01}, journal = {Journal of Plant Physiology}, volume = {238}, pages = {72 - 79}, abstract = {Sodium arsenite (NaAsO2) was especially used as a dormant spray to control grapevine trunk diseases (GTDs) in European vineyards until 2003 when it was banned. It was an efficient product but it was banned due to high risk for human health and the environment. Now, as one of the consequences with climatic changes, GTDs threaten the sustainability of vineyards since no similar and efficacious sprays are presently available to reduce the impact of GTDs. Research efforts were devoted to identify other active ingredients and biological control agents but they remained limited in term of efficacy. New solutions might follow from a better understanding of the modes of action of sodium arsenite which are currently lacking, specially its impact on grapevine physiology. For this study, grafted plants cv. Tempranillo were sprayed by sodium arsenite at the end of the winter. During the vegetative period, the impact on plant physiology was studied by measurement of the photosynthetic activity, the vine growth and development, and some defense responses. Our results showed that arsenic was translocated throughout the vine with an increasing gradient from the leaves to the root system, that photosynthesis was firstly reduced and then stimulated, and that plant tolerance responses were induced especially antioxidant system. The activation of grapevine defense responses by sodium arsenite could be a complementary action to fight fungal pathogens in addition to the fungicide effect.}, keywords = {CMP}, pubstate = {published}, tppubtype = {article} } Sodium arsenite (NaAsO2) was especially used as a dormant spray to control grapevine trunk diseases (GTDs) in European vineyards until 2003 when it was banned. It was an efficient product but it was banned due to high risk for human health and the environment. Now, as one of the consequences with climatic changes, GTDs threaten the sustainability of vineyards since no similar and efficacious sprays are presently available to reduce the impact of GTDs. Research efforts were devoted to identify other active ingredients and biological control agents but they remained limited in term of efficacy. New solutions might follow from a better understanding of the modes of action of sodium arsenite which are currently lacking, specially its impact on grapevine physiology. For this study, grafted plants cv. Tempranillo were sprayed by sodium arsenite at the end of the winter. During the vegetative period, the impact on plant physiology was studied by measurement of the photosynthetic activity, the vine growth and development, and some defense responses. Our results showed that arsenic was translocated throughout the vine with an increasing gradient from the leaves to the root system, that photosynthesis was firstly reduced and then stimulated, and that plant tolerance responses were induced especially antioxidant system. The activation of grapevine defense responses by sodium arsenite could be a complementary action to fight fungal pathogens in addition to the fungicide effect. |
| 109. | C. Demangeat; T. Saied; R. Ramozzi; F. Ingrosso; M. Ruiz‐Lopez; A. Panossian; F. R. Leroux; Y. Fort; C. Comoy Transition‐Metal‐Free Approach for the Direct Arylation of Thiophene: Experimental and Theoretical Investigations towards the (Het)‐Aryne Route Journal Article European Journal of Organic Chemistry 2019, 2019, 547-556. @article{, title = {Transition‐Metal‐Free Approach for the Direct Arylation of Thiophene: Experimental and Theoretical Investigations towards the (Het)‐Aryne Route}, author = {C. Demangeat and T. Saied and R. Ramozzi and F. Ingrosso and M. Ruiz‐Lopez and A. Panossian and F. R. Leroux and Y. Fort and C. Comoy }, url = {https://onlinelibrary.wiley.com/doi/10.1002/ejoc.201801173}, doi = {10.1002/ejoc.201801173}, year = {2019}, date = {2019-01-01}, journal = {European Journal of Organic Chemistry}, volume = {2019}, pages = {547-556}, keywords = {COHA}, pubstate = {published}, tppubtype = {article} } |
2018 |
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| 108. | F.J. Bauer; P.C. Thomas; S.Y. Fouchard; S.J.M. Neunlist High-accuracy prediction of mechanisms of action using structural alerts Journal Article Computational Toxicology 2018, 7, 36-45. @article{, title = {High-accuracy prediction of mechanisms of action using structural alerts}, author = {F.J. Bauer and P.C. Thomas and S.Y. Fouchard and S.J.M. Neunlist}, url = {https://www.sciencedirect.com/science/article/pii/S2468111318300185?via%3Dihub}, doi = {10.1016/j.comtox.2018.06.004}, year = {2018}, date = {2018-12-05}, journal = {Computational Toxicology}, volume = {7}, pages = {36-45}, keywords = {BSM, CRHI}, pubstate = {published}, tppubtype = {article} } |
| 107. | F. Ulm; A.I. Poblador-Bahamonde; S. Choppin; S. Bellemin-Laponnaz M.J. Chetcuti; T. Achard; V. Ritleng Dalton Transactions 2018, 47, 17134-17145 . @article{, title = {Synthesis, characterization, and catalytic application in aldehyde hydrosilylation of half-sandwich nickel complexes bearing (κ1-C)- and hemilabile (κ2-C,S)-thioether-functionalised NHC ligands}, author = {F. Ulm and A.I. Poblador-Bahamonde and S. Choppin and S. Bellemin-Laponnaz M.J. Chetcuti and T. Achard and V. Ritleng}, url = {https://pubs.rsc.org/en/Content/ArticleLanding/2018/DT/C8DT03882A#!divAbstract}, year = {2018}, date = {2018-12-05}, journal = {Dalton Transactions}, volume = {47}, pages = {17134-17145 }, keywords = {COA, SYNCAT}, pubstate = {published}, tppubtype = {article} } |
| 106. | L. Guillemard; F. Colobert; J. Wencel-Delord Visible-Light-Triggered, Metal- and Photocatalyst-Free Acylation of N-Heterocycles Journal Article Advanced Synthesis & Catalysis 2018, 360, 4184-4190. Abstract | Links | Tags: SYNCAT @article{doi:10.1002/adsc.201800692, title = {Visible-Light-Triggered, Metal- and Photocatalyst-Free Acylation of N-Heterocycles}, author = {L. Guillemard and F. Colobert and J. Wencel-Delord}, url = {https://onlinelibrary.wiley.com/doi/abs/10.1002/adsc.201800692}, doi = {10.1002/adsc.201800692}, year = {2018}, date = {2018-11-29}, journal = {Advanced Synthesis & Catalysis}, volume = {360}, number = {21}, pages = {4184-4190}, abstract = {Abstract A photoinduced acylation of N-heterocycles is explored. This visible-light triggered reaction occurs not only under extremely mild reaction conditions, but also does not require the presence of a photosensitizer. The mechanistic studies suggest formation of EDA complexes prompt to harness the energy from visible-light. Compatibility with a large panel of α-keto acids as acyl precursors and an array of N-heterocycles clearly showcase the synthetic potential of this handy and green acylation protocol.}, keywords = {SYNCAT}, pubstate = {published}, tppubtype = {article} } Abstract A photoinduced acylation of N-heterocycles is explored. This visible-light triggered reaction occurs not only under extremely mild reaction conditions, but also does not require the presence of a photosensitizer. The mechanistic studies suggest formation of EDA complexes prompt to harness the energy from visible-light. Compatibility with a large panel of α-keto acids as acyl precursors and an array of N-heterocycles clearly showcase the synthetic potential of this handy and green acylation protocol. |
| 105. | A. Bochicchio; L. Schiavo; L. Chiummiento; P. Lupattelli; M. Funicello; G. Hanquet; S. Choppin; F. Colobert Convergent total synthesis of (±) myricanol, a cyclic natural diarylheptanoid Journal Article Organic & Biomolecular Chemistry 2018, 16, 8859-8869 . @article{, title = {Convergent total synthesis of (±) myricanol, a cyclic natural diarylheptanoid}, author = {A. Bochicchio and L. Schiavo and L. Chiummiento and P. Lupattelli and M. Funicello and G. Hanquet and S. Choppin and F. Colobert}, url = {https://pubs.rsc.org/en/Content/ArticleLanding/2018/OB/C8OB02052C#!divAbstract}, doi = {10.1039/C8OB02052C}, year = {2018}, date = {2018-11-29}, journal = {Organic & Biomolecular Chemistry}, volume = {16}, pages = {8859-8869 }, keywords = {SYNCAT}, pubstate = {published}, tppubtype = {article} } |
| 104. | E. Leoni; J. Mohanraj; M. Holler; M. Mohankumar; I. Nierengarten; F. Monti; A. Sournia-Saquet; B. Delavaux-Nicot; J.-F. Nierengarten; N. Armaroli Inorganic Chemistry 2018, 57, 15537-15549. @article{doi:10.1021/acs.inorgchem.8b02879, title = {Heteroleptic Copper(I) Complexes Prepared from Phenanthroline and Bis-Phosphine Ligands: Rationalization of the Photophysical and Electrochemical Properties}, author = {E. Leoni and J. Mohanraj and M. Holler and M. Mohankumar and I. Nierengarten and F. Monti and A. Sournia-Saquet and B. Delavaux-Nicot and J.-F. Nierengarten and N. Armaroli}, url = {https://doi.org/10.1021/acs.inorgchem.8b02879}, doi = {10.1021/acs.inorgchem.8b02879}, year = {2018}, date = {2018-11-27}, journal = {Inorganic Chemistry}, volume = {57}, number = {24}, pages = {15537-15549}, keywords = {CMM}, pubstate = {published}, tppubtype = {article} } |
| 103. | E. Salomon; M. Schmitt; A. Kumar Marapaka; A. Stamogiannos; G. Revelant; C. Schmitt; S. Alavi; I. Florent; A. Addlagatta; E. Stratikos; C. Tarnus; S. Albrecht Aminobenzosuberone Scaffold as a Modular Chemical Tool for the Inhibition of Therapeutically Relevant M1 Aminopeptidases Journal Article Molecules 2018, 23, 2607. @article{molecules23102607, title = {Aminobenzosuberone Scaffold as a Modular Chemical Tool for the Inhibition of Therapeutically Relevant M1 Aminopeptidases}, author = {E. Salomon and M. Schmitt and A. Kumar Marapaka and A. Stamogiannos and G. Revelant and C. Schmitt and S. Alavi and I. Florent and A. Addlagatta and E. Stratikos and C. Tarnus and S. Albrecht}, url = {http://www.mdpi.com/1420-3049/23/10/2607}, doi = {10.3390/molecules23102607}, issn = {1420-3049}, year = {2018}, date = {2018-10-25}, journal = {Molecules}, volume = {23}, number = {10}, pages = {2607}, abstract = {The synthesis of racemic substituted 7-amino-5,7,8,9-tetrahydrobenzocyclohepten-6-one hydrochlorides was optimized to enhance reproducibility and increase the overall yield. In order to investigate their specificity, series of enzyme inhibition assays were carried out against a diversity of proteases, covering representative members of aspartic, cysteine, metallo and serine endopeptidases and including eight members of the monometallic M1 family of aminopeptidases as well as two members of the bimetallic M17 and M28 aminopeptidase families. This aminobenzosuberone scaffold indeed demonstrated selective inhibition of M1 aminopeptidases to the exclusion of other tested protease families; it was particularly potent against mammalian APN and its bacterial/parasitic orthologues EcPepN and PfAM1.}, keywords = {CMP}, pubstate = {published}, tppubtype = {article} } The synthesis of racemic substituted 7-amino-5,7,8,9-tetrahydrobenzocyclohepten-6-one hydrochlorides was optimized to enhance reproducibility and increase the overall yield. In order to investigate their specificity, series of enzyme inhibition assays were carried out against a diversity of proteases, covering representative members of aspartic, cysteine, metallo and serine endopeptidases and including eight members of the monometallic M1 family of aminopeptidases as well as two members of the bimetallic M17 and M28 aminopeptidase families. This aminobenzosuberone scaffold indeed demonstrated selective inhibition of M1 aminopeptidases to the exclusion of other tested protease families; it was particularly potent against mammalian APN and its bacterial/parasitic orthologues EcPepN and PfAM1. |
| 102. | S. Leroy-Lhez; O. Rezazgui; M. Issawi; M. Elhabiri; C. A. Calliste; C. Riou Why are the anionic porphyrins so efficient to induce plant cell death? A structure-activity relationship study to solve the puzzle Journal Article Journal of Photochemistry and Photobiology A: Chemistry 2018, 368, 276 - 289. @article{LEROYLHEZ2019276, title = {Why are the anionic porphyrins so efficient to induce plant cell death? A structure-activity relationship study to solve the puzzle}, author = {S. Leroy-Lhez and O. Rezazgui and M. Issawi and M. Elhabiri and C. A. Calliste and C. Riou}, url = {http://www.sciencedirect.com/science/article/pii/S1010603018312206}, doi = {https://doi.org/10.1016/j.jphotochem.2018.09.050}, issn = {1010-6030}, year = {2018}, date = {2018-10-25}, journal = {Journal of Photochemistry and Photobiology A: Chemistry}, volume = {368}, pages = {276 - 289}, keywords = {CBM}, pubstate = {published}, tppubtype = {article} } |
| 101. | A. Sutter; M. Elhabiri; G. Ulrich Fluorescent pH-Responsive Probes Based on Water-Soluble Boron-Dipyrromethene (BODIPY) Derivatives, Featuring Long-Wavelength Emission Journal Article Chemistry – A European Journal 2018, 24, 11119-11130. @article{doi:10.1002/chem.201801540, title = {Fluorescent pH-Responsive Probes Based on Water-Soluble Boron-Dipyrromethene (BODIPY) Derivatives, Featuring Long-Wavelength Emission}, author = {A. Sutter and M. Elhabiri and G. Ulrich}, url = {https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201801540}, doi = {10.1002/chem.201801540}, year = {2018}, date = {2018-10-25}, journal = {Chemistry – A European Journal}, volume = {24}, number = {43}, pages = {11119-11130}, abstract = {Abstract We describe here the synthesis of water-soluble red/NIR-emissive, boron-dipyrromethene (BODIPY) derivatives displaying optical (absorption and emission) responses in pH range of 4–8. Substitution close to the tertiary aniline or the phenol subunits selected as the proton-sensitive sites allowed us to finely tune the pH ranges. Furthermore, the introduction of sulfobetaine functions at the boron centre of these pH-responsive BODIPYs afforded valuable fluorescent dyes in the red/NIR region in aqueous media, for which the steric hindrance and electrostatic repulsions prevent their non-emissive aggregation. All the absorption and emission studies, as well as the protonation properties were investigated in aqueous, ethanolic and saline solutions (mimicking physiological conditions). Interestingly, the systems present a fluorescent ratiometric protonation response in EtOH, but the non-protonated form is almost a non-fluorescent species under quasi-physiological conditions (saline aqueous solutions) due to the fading of the emissive character of the low-lying charge-transfer transition in the presence of a supporting electrolyte.}, keywords = {CBM}, pubstate = {published}, tppubtype = {article} } Abstract We describe here the synthesis of water-soluble red/NIR-emissive, boron-dipyrromethene (BODIPY) derivatives displaying optical (absorption and emission) responses in pH range of 4–8. Substitution close to the tertiary aniline or the phenol subunits selected as the proton-sensitive sites allowed us to finely tune the pH ranges. Furthermore, the introduction of sulfobetaine functions at the boron centre of these pH-responsive BODIPYs afforded valuable fluorescent dyes in the red/NIR region in aqueous media, for which the steric hindrance and electrostatic repulsions prevent their non-emissive aggregation. All the absorption and emission studies, as well as the protonation properties were investigated in aqueous, ethanolic and saline solutions (mimicking physiological conditions). Interestingly, the systems present a fluorescent ratiometric protonation response in EtOH, but the non-protonated form is almost a non-fluorescent species under quasi-physiological conditions (saline aqueous solutions) due to the fading of the emissive character of the low-lying charge-transfer transition in the presence of a supporting electrolyte. |
| 100. | X Martin-Benlloch; A Novodomska; D Jacquemin; E Davioud-Charvet; M Elhabiri Iron(iii) coordination properties of ladanein, a flavone lead with a broad-spectrum antiviral activity Journal Article New J. Chem. 2018, 42, 8074-8087. @article{C7NJ04867J, title = {Iron(iii) coordination properties of ladanein, a flavone lead with a broad-spectrum antiviral activity}, author = {X Martin-Benlloch and A Novodomska and D Jacquemin and E Davioud-Charvet and M Elhabiri}, url = {http://dx.doi.org/10.1039/C7NJ04867J}, doi = {10.1039/C7NJ04867J}, year = {2018}, date = {2018-10-25}, journal = {New J. Chem.}, volume = {42}, pages = {8074-8087}, publisher = {The Royal Society of Chemistry}, abstract = {Ladanein, a 5,6,7-trihydroxylayted flavone was recently shown to display potent antiviral activities toward enveloped virus particles (e.g., hepatitis C virus, human immunodeficiency virus, vesicular stomatitis virus). Fe(iii) coordination and pH were suggested to be critical for bioactivation steps triggering host cell entry inhibition. The Fe(iii) complexation properties of ladanein and related analogues, such as negletein and salvigenin, were then studied in solution under quasi-physiological conditions using physico-chemical tools and provided important insights into their stability/reactivity in solution.}, keywords = {CBM}, pubstate = {published}, tppubtype = {article} } Ladanein, a 5,6,7-trihydroxylayted flavone was recently shown to display potent antiviral activities toward enveloped virus particles (e.g., hepatitis C virus, human immunodeficiency virus, vesicular stomatitis virus). Fe(iii) coordination and pH were suggested to be critical for bioactivation steps triggering host cell entry inhibition. The Fe(iii) complexation properties of ladanein and related analogues, such as negletein and salvigenin, were then studied in solution under quasi-physiological conditions using physico-chemical tools and provided important insights into their stability/reactivity in solution. |
| 99. | Q. Dherbassy; J. Wencel-Delord; F. Colobert Atroposelective arylation of biaryls by C-H activation Journal Article Tetrahedron 2018, 74, 6205 - 6212. @article{DHERBASSY20186205, title = {Atroposelective arylation of biaryls by C-H activation}, author = {Q. Dherbassy and J. Wencel-Delord and F. Colobert}, url = {http://www.sciencedirect.com/science/article/pii/S0040402018310317}, doi = {https://doi.org/10.1016/j.tet.2018.08.048}, issn = {0040-4020}, year = {2018}, date = {2018-10-24}, journal = {Tetrahedron}, volume = {74}, number = {43}, pages = {6205 - 6212}, keywords = {SYNCAT}, pubstate = {published}, tppubtype = {article} } |
| 98. | M. Malinowski; R. Hensienne; N. Kern; D. Tardieu; A. Bodlenner; D. Hazelard; P. Compain Stereocontrolled synthesis of polyhydroxylated bicyclic azetidines as a new class of iminosugars Journal Article Organic & Biomolecular Chemistry 2018, 16, 4688-4700. Abstract | Links | Tags: SYBIO @article{C8OB01065J, title = {Stereocontrolled synthesis of polyhydroxylated bicyclic azetidines as a new class of iminosugars}, author = {M. Malinowski and R. Hensienne and N. Kern and D. Tardieu and A. Bodlenner and D. Hazelard and P. Compain}, url = {http://dx.doi.org/10.1039/C8OB01065J}, doi = {10.1039/C8OB01065J}, year = {2018}, date = {2018-10-01}, journal = {Organic & Biomolecular Chemistry}, volume = {16}, pages = {4688-4700}, publisher = {The Royal Society of Chemistry}, abstract = {We report herein the development of a stereodivergent route towards polyhydroxylated bicyclic azetidine scaffolds, namely 6-azabicyclo[3.2.0]heptane derivatives. The strategy hinges on a common bicyclic β-lactam precursor, which is forged by way of a rare example of a cationic Dieckmann-type reaction, followed by IBX-mediated desaturation. Substrate-controlled diastereoselective oxidations then allow the divergent preparation of novel iminosugar mimics.}, keywords = {SYBIO}, pubstate = {published}, tppubtype = {article} } We report herein the development of a stereodivergent route towards polyhydroxylated bicyclic azetidine scaffolds, namely 6-azabicyclo[3.2.0]heptane derivatives. The strategy hinges on a common bicyclic β-lactam precursor, which is forged by way of a rare example of a cationic Dieckmann-type reaction, followed by IBX-mediated desaturation. Substrate-controlled diastereoselective oxidations then allow the divergent preparation of novel iminosugar mimics. |
| 97. | F. Aribi; A. Panossian; J.-P. Vors; S. Pazenok; F. R Leroux 2,4-Bis(fluoroalkyl)quinoline-3-carboxylates as Tools for the Development of Potential Agrochemical Ingredients Journal Article European Journal of Organic Chemistry 2018, 2018, 3792-3802. @article{doi:10.1002/ejoc.201800375, title = {2,4-Bis(fluoroalkyl)quinoline-3-carboxylates as Tools for the Development of Potential Agrochemical Ingredients}, author = {F. Aribi and A. Panossian and J.-P. Vors and S. Pazenok and F. R Leroux}, url = {https://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.201800375}, doi = {10.1002/ejoc.201800375}, year = {2018}, date = {2018-09-13}, journal = {European Journal of Organic Chemistry}, volume = {2018}, number = {27-28}, pages = {3792-3802}, abstract = {Based on an easy and scalable method for the synthesis of quinoline derivatives substituted by fluorinated groups at both the C-2 and C-4 positions developed in our laboratory, we have devised an approach to the synthesis of a new series of unprecedented 2,4-bis(fluoroalkyl)quinoline-3-carboxylates in just two steps. After standard saponification, the latter gave the corresponding 2,4-bis(fluoroalkyl)quinoline-3-carboxylic acids, which served as pivotal intermediates for post-functionalization reactions. Indeed, the carboxylic group could then be derivatized according to known procedures to introduce chemical diversity at the C-3 position of these unprecedented structures. The resulting highly functionalized quinolines can serve as a platform for the development of biologically active molecules with strong potential for agrochemical research.}, keywords = {COHA}, pubstate = {published}, tppubtype = {article} } Based on an easy and scalable method for the synthesis of quinoline derivatives substituted by fluorinated groups at both the C-2 and C-4 positions developed in our laboratory, we have devised an approach to the synthesis of a new series of unprecedented 2,4-bis(fluoroalkyl)quinoline-3-carboxylates in just two steps. After standard saponification, the latter gave the corresponding 2,4-bis(fluoroalkyl)quinoline-3-carboxylic acids, which served as pivotal intermediates for post-functionalization reactions. Indeed, the carboxylic group could then be derivatized according to known procedures to introduce chemical diversity at the C-3 position of these unprecedented structures. The resulting highly functionalized quinolines can serve as a platform for the development of biologically active molecules with strong potential for agrochemical research. |
| 96. | J. Bortoluzzi; V. Jha; G. Levitre; M. J Fer; J. Berreur; G. Masson; A. Panossian; F. R Leroux The Journal of Organic Chemistry 2018, 83, 7751-7761. @article{doi:10.1021/acs.joc.8b00648, title = {Stereoselectivity Switch in the Trapping of Polar Organometallics with Andersen’s Reagent—Access to Highly Stereoenriched Transformable Biphenyls}, author = {J. Bortoluzzi and V. Jha and G. Levitre and M. J Fer and J. Berreur and G. Masson and A. Panossian and F. R Leroux}, url = {https://doi.org/10.1021/acs.joc.8b00648}, doi = {10.1021/acs.joc.8b00648}, year = {2018}, date = {2018-09-13}, journal = {The Journal of Organic Chemistry}, volume = {83}, number = {15}, pages = {7751-7761}, note = {PMID: 29799196}, keywords = {COHA}, pubstate = {published}, tppubtype = {article} } |
| 95. | A. Gómez Herrera; E. Schmitt; A. Panossian; J.-P. Vors; S. Pazenok; F. R Leroux New synthetic access to 3-fluoroalkyl-5-pyrazolecarboxylates and carboxylic acids Journal Article Journal of Fluorine Chemistry 2018, 214, 17 - 23. @article{HERRERA201817, title = {New synthetic access to 3-fluoroalkyl-5-pyrazolecarboxylates and carboxylic acids}, author = {A. Gómez Herrera and E. Schmitt and A. Panossian and J.-P. Vors and S. Pazenok and F. R Leroux}, url = {http://www.sciencedirect.com/science/article/pii/S0022113918302720}, doi = {https://doi.org/10.1016/j.jfluchem.2018.07.010}, issn = {0022-1139}, year = {2018}, date = {2018-09-13}, journal = {Journal of Fluorine Chemistry}, volume = {214}, pages = {17 - 23}, keywords = {COHA}, pubstate = {published}, tppubtype = {article} } |
| 94. | C. Batisse; A. Panossian; G. Hanquet; and F. R. Leroux Access towards enantiopure α,α-difluoromethyl alcohols by means of sulfoxides as traceless chiral auxiliaries Journal Article Chemical Communications 2018, 54, 10423-10426 . @article{, title = {Access towards enantiopure α,α-difluoromethyl alcohols by means of sulfoxides as traceless chiral auxiliaries}, author = {C. Batisse and A. Panossian and G. Hanquet and and F. R. Leroux }, url = {http://pubs.rsc.org/en/content/articlelanding/2018/cc/c8cc05571h#!divAbstract}, doi = {10.1039/C8CC05571H}, year = {2018}, date = {2018-09-13}, journal = {Chemical Communications}, volume = {54}, number = {74}, pages = {10423-10426 }, keywords = {COHA, SYNCAT}, pubstate = {published}, tppubtype = {article} } |
| 93. | V. Le Fouler; G. Duret; P. Bisseret; N. Blanchard Copper-mediated synthesis of N-vinyl ynamides from N-vinyl carbamates Journal Article Tetrahedron Letters 2018, 59, 3349 - 3352. @article{LEFOULER20183349, title = {Copper-mediated synthesis of N-vinyl ynamides from N-vinyl carbamates}, author = {V. Le Fouler and G. Duret and P. Bisseret and N. Blanchard}, url = {http://www.sciencedirect.com/science/article/pii/S0040403918309341}, doi = {https://doi.org/10.1016/j.tetlet.2018.07.053}, issn = {0040-4039}, year = {2018}, date = {2018-09-01}, journal = {Tetrahedron Letters}, volume = {59}, number = {36}, pages = {3349 - 3352}, keywords = {BSM}, pubstate = {published}, tppubtype = {article} } |
| 92. | U. Hahn; E. Maisonhaute; J.-F. Nierengarten Twisted N-Doped Nano-Graphenes: Synthesis, Characterization, and Resolution Journal Article Angewandte Chemie International Edition 2018, 57, 10635-10639. @article{doi:10.1002/anie.201805852, title = {Twisted N-Doped Nano-Graphenes: Synthesis, Characterization, and Resolution}, author = {U. Hahn and E. Maisonhaute and J.-F. Nierengarten}, url = {https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201805852}, doi = {10.1002/anie.201805852}, year = {2018}, date = {2018-08-13}, journal = {Angewandte Chemie International Edition}, volume = {57}, number = {33}, pages = {10635-10639}, abstract = {Abstract Two diastereoisomeric N-doped nanographene derivatives have been efficiently prepared in two synthetic steps starting from an ethynylated hexaazatriphenylene building block. The first derivative adopts a D3-symmetrical propeller-shaped structure with three equivalent nanographene foils. The structure of the second diastereoisomer is C2-symmetrical and differs from the first one by the way two peripheral nanographene foils overlap. Owing to their intertwined structures, the two N-doped nanographenes are soluble in organic solvents and could be characterized by a combination of several analytical tools. Resolution of the D3-symmetrical derivative has been achieved and CD measurements revealed extremely strong Cotton effects.}, keywords = {CMM}, pubstate = {published}, tppubtype = {article} } Abstract Two diastereoisomeric N-doped nanographene derivatives have been efficiently prepared in two synthetic steps starting from an ethynylated hexaazatriphenylene building block. The first derivative adopts a D3-symmetrical propeller-shaped structure with three equivalent nanographene foils. The structure of the second diastereoisomer is C2-symmetrical and differs from the first one by the way two peripheral nanographene foils overlap. Owing to their intertwined structures, the two N-doped nanographenes are soluble in organic solvents and could be characterized by a combination of several analytical tools. Resolution of the D3-symmetrical derivative has been achieved and CD measurements revealed extremely strong Cotton effects. |
| 91. | C. Sambiagio; D. Schönbauer; R. Blieck; T. Dao-Huy; G. Pototschnig; P. Schaaf; T. Wiesinger; M. Farooq Zia; J. Wencel-Delord; T. Besset; B. U. W. Maesa; Michael Schnürch A comprehensive overview of directing groups applied in metal-catalysed C–H functionalisation chemistry Journal Article Chemical Society Reviews 2018, 47, 6603-6743. @article{, title = {A comprehensive overview of directing groups applied in metal-catalysed C–H functionalisation chemistry}, author = {C. Sambiagio and D. Schönbauer and R. Blieck and T. Dao-Huy and G. Pototschnig and P. Schaaf and T. Wiesinger and M. Farooq Zia and J. Wencel-Delord and T. Besset and B. U. W. Maesa and Michael Schnürch }, url = {https://pubs.rsc.org/en/Content/ArticleLanding/2018/CS/C8CS00201K?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FCS+%28RSC+-+Chem.+Soc.+Rev.+latest+articles%29&utm_content=Google+Feedfetcher#!divAbstract}, doi = {10.1039/C8CS00201K}, year = {2018}, date = {2018-07-23}, journal = {Chemical Society Reviews}, volume = {47}, pages = {6603-6743}, keywords = {SYNCAT}, pubstate = {published}, tppubtype = {article} } |
| 90. | X. Zuo; F. Morlet-Savary; M. Schmitt; D. Le Nouën; N. Blanchard; J.-P. Goddard; J. Lalevée Polymer Chemistry 2018, 9, 3952-3958. Abstract | Links | Tags: BSM, CRHI, NMR Mulhouse @article{C8PY00584B, title = {Novel applications of fluorescent brighteners in aqueous visible-light photopolymerization: high performance water-based coating and LED-assisted hydrogel synthesis}, author = {X. Zuo and F. Morlet-Savary and M. Schmitt and D. Le Nouën and N. Blanchard and J.-P. Goddard and J. Lalevée}, url = {http://dx.doi.org/10.1039/C8PY00584B}, doi = {10.1039/C8PY00584B}, year = {2018}, date = {2018-07-17}, journal = {Polymer Chemistry}, volume = {9}, pages = {3952-3958}, publisher = {The Royal Society of Chemistry}, abstract = {Commercial fluorescent brighteners (styrene-based, coumarine-based and 2,5-bis(benzoxazolyl)thiophene-based derivatives) are shown to be active photoinitiators in aqueous visible-light photopolymerization. The proposed systems are characterized by: (i) a low intensity visible-light photopolymerization reaction of acrylates in water using a unique photoinitiating system consisting of a catalytic amount of commercially available optical brighteners and diphenyliodonium salt and (ii) a category of more ecofriendly acrylate formulations enabling the LED-assisted synthesis of hydrogels that typically show high swelling capability. Herein, styrene-based brighteners show their potential as the most promising photoinitiators for the synthesis of tack free waterborne coatings and hydrogels under mild light irradiation conditions, i.e. safe and cheap irradiation devices were selected.}, keywords = {BSM, CRHI, NMR Mulhouse}, pubstate = {published}, tppubtype = {article} } Commercial fluorescent brighteners (styrene-based, coumarine-based and 2,5-bis(benzoxazolyl)thiophene-based derivatives) are shown to be active photoinitiators in aqueous visible-light photopolymerization. The proposed systems are characterized by: (i) a low intensity visible-light photopolymerization reaction of acrylates in water using a unique photoinitiating system consisting of a catalytic amount of commercially available optical brighteners and diphenyliodonium salt and (ii) a category of more ecofriendly acrylate formulations enabling the LED-assisted synthesis of hydrogels that typically show high swelling capability. Herein, styrene-based brighteners show their potential as the most promising photoinitiators for the synthesis of tack free waterborne coatings and hydrogels under mild light irradiation conditions, i.e. safe and cheap irradiation devices were selected. |
| 89. | O. Gavat; T. M. Nguyet Trinh; E. Moulin; T. Ellis; M. Maaloum; E. Buhler; G. Fleith; J.-F. Nierengarten; N. Giuseppone 3D supramolecular self-assembly of [60]fullerene hexaadducts decorated with triarylamine molecules Journal Article Chemical Communications 2018, 55, 7657-7660. @article{, title = {3D supramolecular self-assembly of [60]fullerene hexaadducts decorated with triarylamine molecules}, author = {O. Gavat and T. M. Nguyet Trinh and E. Moulin and T. Ellis and M. Maaloum and E. Buhler and G. Fleith and J.-F. Nierengarten and N. Giuseppone }, url = {http://pubs.rsc.org/en/content/articlelanding/2018/cc/c8cc04079f#!divAbstract}, year = {2018}, date = {2018-07-14}, journal = {Chemical Communications}, volume = {55}, pages = {7657-7660}, keywords = {CMM}, pubstate = {published}, tppubtype = {article} } |
| 88. | D. Tardieu; M. F. Céspedes Dávila; D. Hazelard; P. Compain An Expeditious Synthesis of 1-Thiotrehalose Journal Article Synthesis 2018, 50, 3927-3930. @article{, title = {An Expeditious Synthesis of 1-Thiotrehalose}, author = {D. Tardieu and M. F. Céspedes Dávila and D. Hazelard and P. Compain}, url = {https://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0036-1591595}, doi = {10.1055/s-0036-1591595}, year = {2018}, date = {2018-07-12}, journal = {Synthesis}, volume = {50}, pages = {3927-3930}, keywords = {SYBIO}, pubstate = {published}, tppubtype = {article} } |
| 87. | L. Schiavo; L. Lebedel; P. Massé; S. Choppin; G. Hanquet The Journal of Organic Chemistry 2018, 83, 6247-6258. @article{doi:10.1021/acs.joc.7b02862, title = {Access to Wieland–Miescher Diketone-Derived Building Blocks by Stereoselective Construction of the C-9 Quaternary Carbon Center Using the Mukaiyama Aldol Reaction}, author = {L. Schiavo and L. Lebedel and P. Massé and S. Choppin and G. Hanquet}, url = {https://doi.org/10.1021/acs.joc.7b02862}, doi = {10.1021/acs.joc.7b02862}, year = {2018}, date = {2018-07-08}, journal = {The Journal of Organic Chemistry}, volume = {83}, number = {12}, pages = {6247-6258}, note = {PMID: 29601190}, keywords = {SYNCAT}, pubstate = {published}, tppubtype = {article} } |
| 86. | P. Compain Glycomimetics: Design, Synthesis, and Therapeutic Applications Journal Article Molecules 2018, 23, 1658. Abstract | Links | Tags: SYBIO @article{molecules23071658, title = {Glycomimetics: Design, Synthesis, and Therapeutic Applications}, author = {P. Compain}, url = {http://www.mdpi.com/1420-3049/23/7/1658}, doi = {10.3390/molecules23071658}, issn = {1420-3049}, year = {2018}, date = {2018-07-07}, journal = {Molecules}, volume = {23}, number = {7}, pages = {1658}, abstract = {n/a}, keywords = {SYBIO}, pubstate = {published}, tppubtype = {article} } n/a |
| 85. | E. Howard; A. Cousido-Siah; M. Lepage; J. Schneider; A. Bodlenner; A. Mitschler; A. Meli; I. Izzo; A. Alvarez; A. Podjarny; P. Compain Structural Basis of Outstanding Multivalent Effects in Jack Bean α-Mannosidase Inhibition Journal Article Angewandte Chemie International Edition 2018, 57, 8002-8006. Abstract | Links | Tags: SYBIO @article{doi:10.1002/anie.201801202, title = {Structural Basis of Outstanding Multivalent Effects in Jack Bean α-Mannosidase Inhibition}, author = {E. Howard and A. Cousido-Siah and M. Lepage and J. Schneider and A. Bodlenner and A. Mitschler and A. Meli and I. Izzo and A. Alvarez and A. Podjarny and P. Compain}, url = {https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201801202}, doi = {10.1002/anie.201801202}, year = {2018}, date = {2018-07-02}, journal = {Angewandte Chemie International Edition}, volume = {57}, number = {27}, pages = {8002-8006}, abstract = {Abstract Multivalent design of glycosidase inhibitors is a promising strategy for the treatment of diseases involving enzymatic hydrolysis of glycosidic bonds in carbohydrates. An essential prerequisite for successful applications is the atomic-level understanding of how outstanding binding enhancement occurs with multivalent inhibitors. Herein we report the first high-resolution crystal structures of the Jack bean α-mannosidase (JBα-man) in apo and inhibited states. The three-dimensional structure of JBα-man in complex with the multimeric cyclopeptoid-based inhibitor displaying the largest binding enhancements reported so far provides decisive insight into the molecular mechanisms underlying multivalent effects in glycosidase inhibition.}, keywords = {SYBIO}, pubstate = {published}, tppubtype = {article} } Abstract Multivalent design of glycosidase inhibitors is a promising strategy for the treatment of diseases involving enzymatic hydrolysis of glycosidic bonds in carbohydrates. An essential prerequisite for successful applications is the atomic-level understanding of how outstanding binding enhancement occurs with multivalent inhibitors. Herein we report the first high-resolution crystal structures of the Jack bean α-mannosidase (JBα-man) in apo and inhibited states. The three-dimensional structure of JBα-man in complex with the multimeric cyclopeptoid-based inhibitor displaying the largest binding enhancements reported so far provides decisive insight into the molecular mechanisms underlying multivalent effects in glycosidase inhibition. |
| 84. | J-F Nierengarten; J-P Schneider; T. M. N. Trinh; A. Joosten; M. Holler; M. L. Lepage; A. Bodlenner; I. Garcia-Moreno; C. Ortiz Mellet; P. Compain Giant glycosidase inhibitors: first- and second-generation fullerodendrimers with a dense iminosugar shell. Journal Article Chemistry a European Journal 2018, 24, 2483-2492. @article{, title = {Giant glycosidase inhibitors: first- and second-generation fullerodendrimers with a dense iminosugar shell. }, author = {J-F Nierengarten and J-P Schneider and T. M. N. Trinh and A. Joosten and M. Holler and M. L. Lepage and A. Bodlenner and I. Garcia-Moreno and C. Ortiz Mellet and P. Compain}, doi = {10.1002/chem.201705600 }, year = {2018}, date = {2018-06-14}, journal = {Chemistry a European Journal}, volume = {24}, pages = {2483-2492}, keywords = {CMM, SYBIO}, pubstate = {published}, tppubtype = {article} } |
| 83. | L. Lavaud; S. Pascal; K. Metwally; D. Gasteau; A. Da Silva; Z. Chen; M. Elhabiri; G. Canard,; D. Jacquemin; O. Siri Azacalixphyrins as NIR Photoacoustic Contrast Agents. Journal Article Chemical Communications 2018, 54, 12365. @article{, title = {Azacalixphyrins as NIR Photoacoustic Contrast Agents.}, author = {L. Lavaud and S. Pascal and K. Metwally and D. Gasteau and A. Da Silva and Z. Chen and M. Elhabiri and G. Canard, and D. Jacquemin and O. Siri}, doi = {10.1039/C8CC05851B}, year = {2018}, date = {2018-06-12}, journal = {Chemical Communications}, volume = {54}, pages = {12365}, keywords = {CBM}, pubstate = {published}, tppubtype = {article} } |
| 82. | P. Sidorov; E. Davioud-Charvet; G. Marcou; D. Horvath; A. Varnek AntiMalarial Mode of Action (AMMA) database: data election, verification and chemical space analysis. Journal Article Molecular Informatics 2018, 37,. @article{, title = {AntiMalarial Mode of Action (AMMA) database: data election, verification and chemical space analysis. }, author = {P. Sidorov and E. Davioud-Charvet and G. Marcou and D. Horvath and A. Varnek}, doi = {10.1002/minf.201800021 }, year = {2018}, date = {2018-06-06}, journal = {Molecular Informatics}, volume = {37}, number = {9-10}, keywords = {CBM}, pubstate = {published}, tppubtype = {article} } |
| 81. | E. Meichsner; I. Nierengarten; M. Holler; M. Chessé; J-F Nierengarten A Fullerene-Substituted Pillar[5]arene for the Construction of a Photoactive Rotaxane Journal Article Helvetica Chimica Acta 2018, 101, e1800059. @article{doi:10.1002/hlca.201800059, title = {A Fullerene-Substituted Pillar[5]arene for the Construction of a Photoactive Rotaxane}, author = {E. Meichsner and I. Nierengarten and M. Holler and M. Chessé and J-F Nierengarten }, url = {https://onlinelibrary.wiley.com/doi/abs/10.1002/hlca.201800059}, doi = {10.1002/hlca.201800059}, year = {2018}, date = {2018-05-25}, journal = {Helvetica Chimica Acta}, volume = {101}, number = {6}, pages = {e1800059}, abstract = {Transformation of a methylene group of the pillar[5]arene scaffold into a ketone has been achieved by treatment with N-bromosuccinimide followed by hydrolysis of the bromide intermediate and oxidation of the resulting secondary benzylic alcohol with BaMnO4. Condensation of the resulting macrocycle including a ketone function with p-toluenesulfonyl hydrazide followed by reaction of the corresponding tosylhydrazone with C60 under modified Bamford–Stevens conditions gave a fulleropillar[5]arene derivative. This building block has been used to prepare a rotaxane. The resulting molecule combining the fullerene-functionalized macrocycle with an axle bearing a porphyrin stopper is a photoactive molecular device in which the porphyrin emission is efficiently quenched by the fullerene moiety.}, note = {e1800059 201800059}, keywords = {CMM}, pubstate = {published}, tppubtype = {article} } Transformation of a methylene group of the pillar[5]arene scaffold into a ketone has been achieved by treatment with N-bromosuccinimide followed by hydrolysis of the bromide intermediate and oxidation of the resulting secondary benzylic alcohol with BaMnO4. Condensation of the resulting macrocycle including a ketone function with p-toluenesulfonyl hydrazide followed by reaction of the corresponding tosylhydrazone with C60 under modified Bamford–Stevens conditions gave a fulleropillar[5]arene derivative. This building block has been used to prepare a rotaxane. The resulting molecule combining the fullerene-functionalized macrocycle with an axle bearing a porphyrin stopper is a photoactive molecular device in which the porphyrin emission is efficiently quenched by the fullerene moiety. |
| 80. | D. Meidlinger; L. Marx; C. Bordeianu; S. Choppin; F. Colobert; A. Speicher Access to the Enantiopure Axially Chiral Cyclophane Isoplagiochin D through Atropo-diastereoselective Heck Coupling Journal Article Angewandte Chemie International Edition 2018, 57, 9160-9164. Abstract | Links | Tags: SYNCAT @article{doi:10.1002/anie.201803677, title = {Access to the Enantiopure Axially Chiral Cyclophane Isoplagiochin D through Atropo-diastereoselective Heck Coupling}, author = {D. Meidlinger and L. Marx and C. Bordeianu and S. Choppin and F. Colobert and A. Speicher}, url = {https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201803677}, doi = {10.1002/anie.201803677}, year = {2018}, date = {2018-05-23}, journal = {Angewandte Chemie International Edition}, volume = {57}, number = {29}, pages = {9160-9164}, abstract = {Abstract Macrocyclization is typically the key step in the syntheses of cyclophane-type natural products. Considering cyclophanes with axially chiral biaryl moieties, the control of atroposelectivity is essential with biological activity and is synthetically challenging. We report an atroposelective approach involving Heck cyclization, which for the first time enables the total synthesis of an enantiopure macrocyclic bis(bibenzyl), namely isoplagiochin D. An enantiopure sulfinyl auxiliary in the ortho position of a biaryl axis (still flexible) was used to induce an atropo-diastereoselective Heck coupling (up to 98 % de). The traceless character of the sulfinyl auxiliary enables the introduction of a hydroxy group to give the target molecule with 98 % ee as well.}, keywords = {SYNCAT}, pubstate = {published}, tppubtype = {article} } Abstract Macrocyclization is typically the key step in the syntheses of cyclophane-type natural products. Considering cyclophanes with axially chiral biaryl moieties, the control of atroposelectivity is essential with biological activity and is synthetically challenging. We report an atroposelective approach involving Heck cyclization, which for the first time enables the total synthesis of an enantiopure macrocyclic bis(bibenzyl), namely isoplagiochin D. An enantiopure sulfinyl auxiliary in the ortho position of a biaryl axis (still flexible) was used to induce an atropo-diastereoselective Heck coupling (up to 98 % de). The traceless character of the sulfinyl auxiliary enables the introduction of a hydroxy group to give the target molecule with 98 % ee as well. |
| 79. | P. Bisseret; H. Abdelkafi; N. Blanchard Aryl transition metal chemical warheads for protein bioconjugation Journal Article Chemical Science 2018, 9, 5132-5144. @article{C8SC00780B, title = {Aryl transition metal chemical warheads for protein bioconjugation}, author = {P. Bisseret and H. Abdelkafi and N. Blanchard}, url = {http://dx.doi.org/10.1039/C8SC00780B}, doi = {10.1039/C8SC00780B}, year = {2018}, date = {2018-05-22}, journal = {Chemical Science}, volume = {9}, pages = {5132-5144}, publisher = {The Royal Society of Chemistry}, abstract = {The past seven years have witnessed the burgeoning of protein bioconjugation reactions highlighting aryl transition metal reagents as coupling partners. This new bioorthogonal organometallic chemistry, which sets the scene for stoichiometric processes in place of the catalytic procedures that developed in parallel, already enabled the forging of C-S and C-C bonds onto protein substrates, respectively in their native state or equipped with pre-installed non-natural terminal alkene or alkyne appendages. Although not yet applied to proteins, related transformations pointing to the creation of C-N bonds have, in addition, just been disclosed by targeting peptide lysine residues. Central to this research was the selection of ligands attached to the transition metal, in order to confer to metal complexes, not only their stability in aqueous medium, but also the desired chemoselectivity. We summarize here this body of work, which has already put in the limelight elaborated palladium and gold complexes equipped with biologically relevant appendages, such as fluorescent and affinity tags, as well as drug molecules. This research holds much promise, not only for the study of proteins themselves, but also for the design of new protein-based biotherapeutics, such as protein-drug conjugates or constrained analogs resulting from macrocyclisation reactions.}, keywords = {BSM}, pubstate = {published}, tppubtype = {article} } The past seven years have witnessed the burgeoning of protein bioconjugation reactions highlighting aryl transition metal reagents as coupling partners. This new bioorthogonal organometallic chemistry, which sets the scene for stoichiometric processes in place of the catalytic procedures that developed in parallel, already enabled the forging of C-S and C-C bonds onto protein substrates, respectively in their native state or equipped with pre-installed non-natural terminal alkene or alkyne appendages. Although not yet applied to proteins, related transformations pointing to the creation of C-N bonds have, in addition, just been disclosed by targeting peptide lysine residues. Central to this research was the selection of ligands attached to the transition metal, in order to confer to metal complexes, not only their stability in aqueous medium, but also the desired chemoselectivity. We summarize here this body of work, which has already put in the limelight elaborated palladium and gold complexes equipped with biologically relevant appendages, such as fluorescent and affinity tags, as well as drug molecules. This research holds much promise, not only for the study of proteins themselves, but also for the design of new protein-based biotherapeutics, such as protein-drug conjugates or constrained analogs resulting from macrocyclisation reactions. |
| 78. | Q. Dherbassy; J.-P. Djukic; J. Wencel‐Delord; F. Colobert Two Stereoinduction Events in One C−H Activation Step: A Route towards Terphenyl Ligands with Two Atropisomeric Axes Journal Article Angewandte Chemie 2018, 130, 4758-4762. Abstract | Links | Tags: SYNCAT @article{doi:10.1002/ange.201801130, title = {Two Stereoinduction Events in One C−H Activation Step: A Route towards Terphenyl Ligands with Two Atropisomeric Axes}, author = {Q. Dherbassy and J.-P. Djukic and J. Wencel‐Delord and F. Colobert }, url = {https://onlinelibrary.wiley.com/doi/abs/10.1002/ange.201801130}, doi = {10.1002/ange.201801130}, year = {2018}, date = {2018-05-02}, journal = {Angewandte Chemie}, volume = {130}, number = {17}, pages = {4758-4762}, abstract = {Abstract Herein we disclose the synthesis of original chiral scaffolds—ortho‐orientated terphenyls presenting two atropisomeric Ar–Ar axes. These unusual structures were built up by using the C−H activation approach, and remarkably, both chiral axes were controlled with excellent stereoselectivity in a single transformation. During the reaction, not only does atroposelective functionalization of a biaryl precursor occur to establish one stereogenic axis, but an unprecedented atropo‐stereoselective C−H arylation also takes place to generate the second stereogenic element. These enantiomerically pure ortho‐terphenyls show an original tridimensional structure and thus constitute a unique foundation for building up a library of enantiomerically pure bidentate ligands, such as the new ligands S/N‐Biax and diphosphine BiaxPhos.}, keywords = {SYNCAT}, pubstate = {published}, tppubtype = {article} } Abstract Herein we disclose the synthesis of original chiral scaffolds—ortho‐orientated terphenyls presenting two atropisomeric Ar–Ar axes. These unusual structures were built up by using the C−H activation approach, and remarkably, both chiral axes were controlled with excellent stereoselectivity in a single transformation. During the reaction, not only does atroposelective functionalization of a biaryl precursor occur to establish one stereogenic axis, but an unprecedented atropo‐stereoselective C−H arylation also takes place to generate the second stereogenic element. These enantiomerically pure ortho‐terphenyls show an original tridimensional structure and thus constitute a unique foundation for building up a library of enantiomerically pure bidentate ligands, such as the new ligands S/N‐Biax and diphosphine BiaxPhos. |
| 77. | C. Selvam; I. A Lemasson; I. Brabet; N. Oueslati; B. Karaman; A. Cabaye; A. S Tora; B. Commare; T. Courtiol; S. Cesarini; I. McCort-Tranchepain; D. Rigault; L. Mony; T. Bessiron; H. McLean; F. R Leroux; F. Colobert; H. Daniel; A. Goupil-Lamy; H.-O. Bertrand; C. Goudet; J.-P. Pin; F. C Acher Increased Potency and Selectivity for Group III Metabotropic Glutamate Receptor Agonists Binding at Dual sites Journal Article Journal of Medicinal Chemistry 2018, 61, 1969-1989. @article{doi:10.1021/acs.jmedchem.7b01438, title = {Increased Potency and Selectivity for Group III Metabotropic Glutamate Receptor Agonists Binding at Dual sites}, author = {C. Selvam and I. A Lemasson and I. Brabet and N. Oueslati and B. Karaman and A. Cabaye and A. S Tora and B. Commare and T. Courtiol and S. Cesarini and I. McCort-Tranchepain and D. Rigault and L. Mony and T. Bessiron and H. McLean and F. R Leroux and F. Colobert and H. Daniel and A. Goupil-Lamy and H.-O. Bertrand and C. Goudet and J.-P. Pin and F. C Acher}, url = {https://doi.org/10.1021/acs.jmedchem.7b01438}, doi = {10.1021/acs.jmedchem.7b01438}, year = {2018}, date = {2018-05-01}, journal = {Journal of Medicinal Chemistry}, volume = {61}, number = {5}, pages = {1969-1989}, note = {PMID: 29397723}, keywords = {COHA, SYNCAT}, pubstate = {published}, tppubtype = {article} } |
| 76. | H. Norouzi-Arasi; X. J. Salom-Roig; S.Lanners; G. Hanquet First Total Synthesis of Pamamycin-621D Journal Article Current Organic Synthesis 2018, 15, 105-109. @article{, title = {First Total Synthesis of Pamamycin-621D}, author = {H. Norouzi-Arasi and X. J. Salom-Roig and S.Lanners and G. Hanquet}, doi = {10.2174/1570179414666170525103947}, year = {2018}, date = {2018-04-25}, journal = {Current Organic Synthesis}, volume = {15}, pages = {105-109}, keywords = {SYNCAT}, pubstate = {published}, tppubtype = {article} } |
| 75. | A. Chemtob; N. Feillée; C. Ley; A. Ponche; S. Rigolet; C. Soraru; L. Ploux; D. Le Nouen Oxidative photopolymerization of thiol-terminated polysulfide resins. Application in antibacterial coatings Journal Article Progress in Organic Coatings 2018, 121, 80 - 88. Abstract | Links | Tags: NMR Mulhouse @article{Chemtob201880, title = {Oxidative photopolymerization of thiol-terminated polysulfide resins. Application in antibacterial coatings}, author = {A. Chemtob and N. Feillée and C. Ley and A. Ponche and S. Rigolet and C. Soraru and L. Ploux and D. Le Nouen}, url = {https://www.sciencedirect.com/science/article/pii/S0300944018300511}, doi = {https://doi.org/10.1016/j.porgcoat.2018.04.017}, issn = {0300-9440}, year = {2018}, date = {2018-04-25}, journal = {Progress in Organic Coatings}, volume = {121}, pages = {80 - 88}, abstract = {Abstract A UV photoinduced cross-linking of non-modified commercial poly(disulfide) resins (Thioplast) is reported via the air oxidative photocoupling of terminal thiol functions. Catalyzed by a photogenerated guanidine base (TBD), this step-growth photopolymerization is useful to maximize disulfide functions content. The mechanism proceeds through thiol deprotonation into thiolate anions, further oxidized into thiyl radicals, eventually dimerizing into disulfide cross-links. Starting with a detailed structural characterization of the thiol-terminated resin, photooxidative kinetics are studied under exposure to a polychromatic medium-pressure Hg arc using Raman and infrared spectroscopy. The effects of irradiance, film thickness, photobase concentration, resin molar mass, and content of an additional polythiol monomer (reactive diluent) have been investigated. In an effort of upscaling, irradiation under a 365 nm LED panel has enabled the fast preparation of 1.5 μm thick cross-linked poly(disulfide) coatings in a matter of minutes. Capitalizing on the ability of residual thiol groups to react with silver cations, a post-functionalization has been successfully performed, leading to films exhibiting at their surface stable thiolate-silver bonds as proved by X-ray photoelectron spectroscopy. Despite the well-established biocide action of silver ions, no antibacterial action has been evidenced by confocal fluorescence microscopy because of insufficient release.}, keywords = {NMR Mulhouse}, pubstate = {published}, tppubtype = {article} } Abstract A UV photoinduced cross-linking of non-modified commercial poly(disulfide) resins (Thioplast) is reported via the air oxidative photocoupling of terminal thiol functions. Catalyzed by a photogenerated guanidine base (TBD), this step-growth photopolymerization is useful to maximize disulfide functions content. The mechanism proceeds through thiol deprotonation into thiolate anions, further oxidized into thiyl radicals, eventually dimerizing into disulfide cross-links. Starting with a detailed structural characterization of the thiol-terminated resin, photooxidative kinetics are studied under exposure to a polychromatic medium-pressure Hg arc using Raman and infrared spectroscopy. The effects of irradiance, film thickness, photobase concentration, resin molar mass, and content of an additional polythiol monomer (reactive diluent) have been investigated. In an effort of upscaling, irradiation under a 365 nm LED panel has enabled the fast preparation of 1.5 μm thick cross-linked poly(disulfide) coatings in a matter of minutes. Capitalizing on the ability of residual thiol groups to react with silver cations, a post-functionalization has been successfully performed, leading to films exhibiting at their surface stable thiolate-silver bonds as proved by X-ray photoelectron spectroscopy. Despite the well-established biocide action of silver ions, no antibacterial action has been evidenced by confocal fluorescence microscopy because of insufficient release. |
| 74. | B. Delavaux-Nicot; H. Ben Aziza; I. Nierengarten; T. Minh Nguyet Trinh; E. Meichsner; M. Chessé; M. Holler; R. Abidi; E. Maisonhaute; J.-F. Nierengarten A Rotaxane Scaffold for the Construction of Multiporphyrinic Light-Harvesting Devices Journal Article Chemistry - A European Journal 2018, 24, 133-140. @article{DelavauxNicot:2018iw, title = {A Rotaxane Scaffold for the Construction of Multiporphyrinic Light-Harvesting Devices}, author = {B. Delavaux-Nicot and H. Ben Aziza and I. Nierengarten and T. Minh Nguyet Trinh and E. Meichsner and M. Chessé and M. Holler and R. Abidi and E. Maisonhaute and J.-F. Nierengarten}, doi = {10.1002/chem.201704124}, year = {2018}, date = {2018-04-24}, journal = {Chemistry - A European Journal}, volume = {24}, number = {1}, pages = {133-140}, keywords = {CMM}, pubstate = {published}, tppubtype = {article} } |
| 73. | I. Nierengarten; E. Meichsner; M. Holler; P. Pieper; R. Deschenaux; B. Delavaux-Nicot; J.-F. Nierengarten Preparation of Pillar[5]arene-Based [2]Rotaxanes by a Stopper-Exchange Strategy Journal Article Chemistry - A European Journal 2018, 24, 169-177. @article{Nierengarten:2018kg, title = {Preparation of Pillar[5]arene-Based [2]Rotaxanes by a Stopper-Exchange Strategy}, author = {I. Nierengarten and E. Meichsner and M. Holler and P. Pieper and R. Deschenaux and B. Delavaux-Nicot and J.-F. Nierengarten}, doi = {10.1002/chem.201703997}, year = {2018}, date = {2018-04-24}, journal = {Chemistry - A European Journal}, volume = {24}, number = {1}, pages = {169-177}, keywords = {CMM}, pubstate = {published}, tppubtype = {article} } |
| 72. | F. Aribi; A. Panossian; D. Jacquemin; J.-P. Vors; S. Pazenok; F. R Leroux; M. Elhabiri A physico-chemical investigation of fluorine-enriched quinolines Journal Article New J. Chem. 2018, 42, 10036-10047. Abstract | Links | Tags: CBM, COHA @article{C8NJ00916C, title = {A physico-chemical investigation of fluorine-enriched quinolines}, author = {F. Aribi and A. Panossian and D. Jacquemin and J.-P. Vors and S. Pazenok and F. R Leroux and M. Elhabiri}, url = {http://dx.doi.org/10.1039/C8NJ00916C}, doi = {10.1039/C8NJ00916C}, year = {2018}, date = {2018-04-23}, journal = {New J. Chem.}, volume = {42}, pages = {10036-10047}, publisher = {The Royal Society of Chemistry}, abstract = {Quinoline derivatives bearing fluoroalkyl groups at both 2 and 4 positions are scarcely described in the literature. Nevertheless, the addition of fluorine onto the quinoline core might bring about new interesting physico-chemical properties. To confirm this hypothesis a homogenous series of 2,4-bis(fluoroalkyl)-substituted quinolines was synthesized under mild reaction conditions and their physico-chemical properties were thoroughly investigated by various techniques to illustrate their potential usefulness as new building blocks for applications ranging from organic chemistry to materials science.}, keywords = {CBM, COHA}, pubstate = {published}, tppubtype = {article} } Quinoline derivatives bearing fluoroalkyl groups at both 2 and 4 positions are scarcely described in the literature. Nevertheless, the addition of fluorine onto the quinoline core might bring about new interesting physico-chemical properties. To confirm this hypothesis a homogenous series of 2,4-bis(fluoroalkyl)-substituted quinolines was synthesized under mild reaction conditions and their physico-chemical properties were thoroughly investigated by various techniques to illustrate their potential usefulness as new building blocks for applications ranging from organic chemistry to materials science. |
| 71. | L. Feng; D. A. Lanfranchi; L. Cotos; E. Cesar-Rodo; K. Ehrhardt; A.-A. Goetz; H. Zimmermann; F. Fenaille; S. A Blandin; E. Davioud-Charvet Synthesis of plasmodione metabolites and 13C-enriched plasmodione as chemical tools for drug metabolism investigation Journal Article Organic & Biomolecular Chemistry 2018, 16, 2647-2665. @article{C8OB00227D, title = {Synthesis of plasmodione metabolites and 13C-enriched plasmodione as chemical tools for drug metabolism investigation}, author = {L. Feng and D. A. Lanfranchi and L. Cotos and E. Cesar-Rodo and K. Ehrhardt and A.-A. Goetz and H. Zimmermann and F. Fenaille and S. A Blandin and E. Davioud-Charvet}, url = {http://dx.doi.org/10.1039/C8OB00227D}, doi = {10.1039/C8OB00227D}, year = {2018}, date = {2018-04-21}, journal = {Organic & Biomolecular Chemistry}, volume = {16}, pages = {2647-2665}, publisher = {The Royal Society of Chemistry}, abstract = {Malaria is a tropical parasitic disease threatening populations in tropical and sub-tropical areas. Resistance to antimalarial drugs has spread all over the world in the past 50 years, thus new drugs are urgently needed. Plasmodione (benzylmenadione series) has been identified as a potent antimalarial early lead drug, acting through a redox bioactivation on asexual and young sexual blood stages. To investigate its metabolism, a series of plasmodione-based tools, including a fully 13C-labelled lead drug and putative metabolites, have been designed and synthesized for drug metabolism investigation. Furthermore, with the help of UHPLC-MS/MS, two of the drug metabolites have been identified from urine of drug-treated mice.}, keywords = {CBM}, pubstate = {published}, tppubtype = {article} } Malaria is a tropical parasitic disease threatening populations in tropical and sub-tropical areas. Resistance to antimalarial drugs has spread all over the world in the past 50 years, thus new drugs are urgently needed. Plasmodione (benzylmenadione series) has been identified as a potent antimalarial early lead drug, acting through a redox bioactivation on asexual and young sexual blood stages. To investigate its metabolism, a series of plasmodione-based tools, including a fully 13C-labelled lead drug and putative metabolites, have been designed and synthesized for drug metabolism investigation. Furthermore, with the help of UHPLC-MS/MS, two of the drug metabolites have been identified from urine of drug-treated mice. |
| 70. | Maria F Céspedes Dávila; Jérémy P Schneider; Amélie Godard; Damien Hazelard; Philippe Compain One-Pot, Highly Stereoselective Synthesis of Dithioacetal-α,α-Diglycosides Journal Article Molecules 2018, 23, 914. Abstract | Links | Tags: SYBIO @article{molecules23040914, title = {One-Pot, Highly Stereoselective Synthesis of Dithioacetal-α,α-Diglycosides}, author = {Maria F Céspedes Dávila and Jérémy P Schneider and Amélie Godard and Damien Hazelard and Philippe Compain}, url = {http://www.mdpi.com/1420-3049/23/4/914}, doi = {10.3390/molecules23040914}, issn = {1420-3049}, year = {2018}, date = {2018-04-15}, journal = {Molecules}, volume = {23}, number = {4, ARTICLE NUMBER = 914}, pages = {914}, abstract = {A one-step access to dithioacetal-α,α-diglycosides is reported. The synthetic strategy is based on the thioacetalization of aldehydes or ketones via highly stereoselective ring-opening of 1,6 anhydrosugars with bis(trimethylsilyl)sulfide.}, keywords = {SYBIO}, pubstate = {published}, tppubtype = {article} } A one-step access to dithioacetal-α,α-diglycosides is reported. The synthetic strategy is based on the thioacetalization of aldehydes or ketones via highly stereoselective ring-opening of 1,6 anhydrosugars with bis(trimethylsilyl)sulfide. |
| 69. | Maeva M Pichon; Fabien Stauffert; Luis G Addante-Moya; Anne Bodlenner; Philippe Compain Metal-Free Iodine-Mediated Deoxygenation of Alcohols in the Position to Electron-Withdrawing Groups Journal Article European Journal of Organic Chemistry 2018, 1538-1545. @article{ISI:000430003600004, title = {Metal-Free Iodine-Mediated Deoxygenation of Alcohols in the Position to Electron-Withdrawing Groups}, author = {Maeva M Pichon and Fabien Stauffert and Luis G Addante-Moya and Anne Bodlenner and Philippe Compain}, doi = {10.1002/ejoc.201800051}, issn = {1434-193X}, year = {2018}, date = {2018-04-01}, journal = {European Journal of Organic Chemistry}, number = {13}, pages = {1538-1545}, keywords = {SYBIO}, pubstate = {published}, tppubtype = {article} } |
| 68. | E Stempien; M -L Goddard; Y Leva; M Bénard-Gellon; H Laloue; S Farine; F Kieffer-Mazet; C Tarnus; C Bertsch; J Chong Protoplasma 2018, 255, 613–628. @article{Stempien2018, title = {Secreted proteins produced by fungi associated with Botryosphaeria dieback trigger distinct defense responses in Vitis vinifera and Vitis rupestris cells}, author = {E Stempien and M -L Goddard and Y Leva and M Bénard-Gellon and H Laloue and S Farine and F Kieffer-Mazet and C Tarnus and C Bertsch and J Chong}, url = {https://doi.org/10.1007/s00709-017-1175-z}, doi = {10.1007/s00709-017-1175-z}, issn = {1615-6102}, year = {2018}, date = {2018-03-01}, journal = {Protoplasma}, volume = {255}, number = {2}, pages = {613--628}, abstract = {Grapevine trunk diseases (Eutypa dieback, esca and Botryosphaeria dieback) are caused by a complex of xylem-inhabiting fungi, which severely reduce yields in vineyards. Botryosphaeria dieback is associated with Botryosphaeriaceae. In order to develop effective strategies against Botryosphaeria dieback, we investigated the molecular basis of grapevine interactions with a virulent species, Neofusicoccum parvum, and a weak pathogen, Diplodia seriata. We investigated defenses induced by purified secreted fungal proteins within suspension cells of Vitis (Vitis rupestris and Vitis vinifera cv. Gewurztraminer) with putative different susceptibility to Botryosphaeria dieback. Our results show that Vitis cells are able to detect secreted proteins produced by Botryosphaeriaceae, resulting in a rapid alkalinization of the extracellular medium and the production of reactive oxygen species. Concerning early defense responses, N. parvum proteins induced a more intense response compared to D. seriata. Early and late defense responses, i.e., extracellular medium alkalinization, cell death, and expression of PR defense genes were stronger in V. rupestris compared to V. vinifera, except for stilbene production. Secreted Botryosphaeriaceae proteins triggered a high accumulation of $delta$-viniferin in V. vinifera suspension cells. Artificial inoculation assays on detached canes with N. parvum and D. seriata showed that the development of necrosis is reduced in V. rupestris compared to V. vinifera cv. Gewurztraminer. This may be related to a more efficient induction of defense responses in V. rupestris, although not sufficient to completely inhibit fungal colonization. Overall, our work shows a specific signature of defense responses depending on the grapevine genotype and the fungal species.}, keywords = {CMP}, pubstate = {published}, tppubtype = {article} } Grapevine trunk diseases (Eutypa dieback, esca and Botryosphaeria dieback) are caused by a complex of xylem-inhabiting fungi, which severely reduce yields in vineyards. Botryosphaeria dieback is associated with Botryosphaeriaceae. In order to develop effective strategies against Botryosphaeria dieback, we investigated the molecular basis of grapevine interactions with a virulent species, Neofusicoccum parvum, and a weak pathogen, Diplodia seriata. We investigated defenses induced by purified secreted fungal proteins within suspension cells of Vitis (Vitis rupestris and Vitis vinifera cv. Gewurztraminer) with putative different susceptibility to Botryosphaeria dieback. Our results show that Vitis cells are able to detect secreted proteins produced by Botryosphaeriaceae, resulting in a rapid alkalinization of the extracellular medium and the production of reactive oxygen species. Concerning early defense responses, N. parvum proteins induced a more intense response compared to D. seriata. Early and late defense responses, i.e., extracellular medium alkalinization, cell death, and expression of PR defense genes were stronger in V. rupestris compared to V. vinifera, except for stilbene production. Secreted Botryosphaeriaceae proteins triggered a high accumulation of $delta$-viniferin in V. vinifera suspension cells. Artificial inoculation assays on detached canes with N. parvum and D. seriata showed that the development of necrosis is reduced in V. rupestris compared to V. vinifera cv. Gewurztraminer. This may be related to a more efficient induction of defense responses in V. rupestris, although not sufficient to completely inhibit fungal colonization. Overall, our work shows a specific signature of defense responses depending on the grapevine genotype and the fungal species. |
| 67. | James Rae; Johanna Frey; Soufyan Jerhaoui; Sabine Choppin; Joanna Wencel-Delord; Françoise Colobert Synthesis of Axially Chiral C–N Scaffolds via Asymmetric Coupling with Enantiopure Sulfinyl Iodanes Journal Article ACS Catalysis 2018, 8, 2805-2809. @article{doi:10.1021/acscatal.7b04343, title = {Synthesis of Axially Chiral C–N Scaffolds via Asymmetric Coupling with Enantiopure Sulfinyl Iodanes}, author = {James Rae and Johanna Frey and Soufyan Jerhaoui and Sabine Choppin and Joanna Wencel-Delord and Françoise Colobert}, url = {https://doi.org/10.1021/acscatal.7b04343}, doi = {10.1021/acscatal.7b04343}, year = {2018}, date = {2018-02-02}, journal = {ACS Catalysis}, volume = {8}, number = {4}, pages = {2805-2809}, keywords = {SYNCAT}, pubstate = {published}, tppubtype = {article} } |
| 66. | B. de P. Cardoso, S. Shahane, J.-M. Bernard-Schaaf, L. F. Veiros, M. J. Chetcuti, V. Ritleng Dalton Transactions 2018, 47, 1535-1547. @article{, title = {Displacement of η5-cyclopentadienyl ligands from half-sandwich C,C-(NHC-cyanoalkyl)–nickel(II) metallacycles: further insight into the structure of the resulting Cp-free nickelacycles and a catalytic activity study}, author = {B. de P. Cardoso, S. Shahane, J.-M. Bernard-Schaaf, L. F. Veiros, M. J. Chetcuti, V. Ritleng}, doi = {10.1039/C7DT04560C}, year = {2018}, date = {2018-02-01}, journal = {Dalton Transactions}, volume = {47}, pages = {1535-1547}, keywords = {COA}, pubstate = {published}, tppubtype = {article} } |
| 65. | D. Edouard; L. Lefebvre; L. Jierry; V. Ritleng; J. Kelber Reduction kit, reducing composition and use of said kit and composition Patent WO 2018020146 A1, 2018,. @patent{, title = {Reduction kit, reducing composition and use of said kit and composition}, author = {D. Edouard and L. Lefebvre and L. Jierry and V. Ritleng and J. Kelber}, url = {https://worldwide.espacenet.com/publicationDetails/biblio?DB=EPODOC&II=0&ND=3&adjacent=true&locale=en_EP&FT=D&date=20180201&CC=WO&NR=2018020146A1&KC=A1}, year = {2018}, date = {2018-02-01}, number = {WO 2018020146 A1}, keywords = {COA}, pubstate = {published}, tppubtype = {patent} } |
| 64. | Steffenhagen M.; Latus A.; T. T. Minh Nguyet; Nierengarten I.; Lucas I. T.; Joiret S.; Landoulsi J.; Delavaux‐Nicot B.; Nierengarten J.‐F.; Maisonhaute E. A Rotaxane Scaffold Bearing Multiple Redox Centers: Synthesis, Surface Modification and Electrochemical Properties Journal Article Chemistry – A European Journal 2018, 24, 1701-1708. @article{doi:10.1002/chem.201705245, title = {A Rotaxane Scaffold Bearing Multiple Redox Centers: Synthesis, Surface Modification and Electrochemical Properties}, author = {Steffenhagen M. and Latus A. and T. T. Minh Nguyet and Nierengarten I. and Lucas I. T. and Joiret S. and Landoulsi J. and Delavaux‐Nicot B. and Nierengarten J.‐F. and Maisonhaute E.}, url = {https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201705245}, doi = {10.1002/chem.201705245}, year = {2018}, date = {2018-02-01}, journal = {Chemistry – A European Journal}, volume = {24}, number = {7}, pages = {1701-1708}, abstract = {Abstract A rotaxane scaffold incorporating two dithiolane anchoring units for the modification of gold surfaces has been functionalized with multiple copies of a redox unit, namely ferrocene. Surface modification has been first assessed at the single molecule level by atomic force microscopy (AFM) and scanning tunneling microscopy (STM) imaging, while tip enhanced Raman spectroscopy (TERS) provided the local vibrational signature of the ferrocenyl subunits of the rotaxanes grafted onto the gold surface. Finally, oxidation of the redox moieties within a rotaxane scaffold grafted onto gold microelectrodes has been investigated by ultrafast cyclic voltammetry. Intramolecular electron hopping is indeed extremely fast in this system. Moreover, the kinetics of charge injection depends on the molecular coverage due to the influence of intermolecular contacts on molecular motions.}, keywords = {CMM}, pubstate = {published}, tppubtype = {article} } Abstract A rotaxane scaffold incorporating two dithiolane anchoring units for the modification of gold surfaces has been functionalized with multiple copies of a redox unit, namely ferrocene. Surface modification has been first assessed at the single molecule level by atomic force microscopy (AFM) and scanning tunneling microscopy (STM) imaging, while tip enhanced Raman spectroscopy (TERS) provided the local vibrational signature of the ferrocenyl subunits of the rotaxanes grafted onto the gold surface. Finally, oxidation of the redox moieties within a rotaxane scaffold grafted onto gold microelectrodes has been investigated by ultrafast cyclic voltammetry. Intramolecular electron hopping is indeed extremely fast in this system. Moreover, the kinetics of charge injection depends on the molecular coverage due to the influence of intermolecular contacts on molecular motions. |
| 63. | E. Schmitt; B. Commare; A. Panossian; J.-P. Vors; S. Pazenok; F. R. Leroux Chemistry A European Journal 2018, 24, 1311-1316. @article{, title = {Synthesis of Mono- and Bis(fluoroalkyl)pyrimidines from FARs, Fluorinated Acetoacetates, and Malononitrile Provides Easy Access to Novel High-Value Pyrimidine Scaffolds}, author = {E. Schmitt and B. Commare and A. Panossian and J.-P. Vors and S. Pazenok and F. R. Leroux}, doi = {10.1002/chem.201703982}, year = {2018}, date = {2018-01-26}, journal = {Chemistry A European Journal}, volume = {24}, pages = {1311-1316}, keywords = {COHA}, pubstate = {published}, tppubtype = {article} } |
| 62. | L Ronchi; A Ryzhikov; H Nouali; T J Daou; S Albrecht; J Patarin Extra large pore opening CFI and DON-type zeosils for mechanical energy storage Journal Article Microporous and Mesoporous Materials 2018, 255, 211-219. @article{Ronchi2018211, title = {Extra large pore opening CFI and DON-type zeosils for mechanical energy storage}, author = {L Ronchi and A Ryzhikov and H Nouali and T J Daou and S Albrecht and J Patarin}, url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-85026455604&doi=10.1016%2fj.micromeso.2017.07.039&partnerID=40&md5=15026ed09680c4e4bafd035766700e33}, doi = {10.1016/j.micromeso.2017.07.039}, year = {2018}, date = {2018-01-01}, journal = {Microporous and Mesoporous Materials}, volume = {255}, pages = {211-219}, note = {cited By 0}, keywords = {CMP}, pubstate = {published}, tppubtype = {article} } |
| 61. | S. Jerhaoui; P. Poutrel; J.-P. Djukic; J. Wencel-Delord; F. Colobert Stereospecific C-H activation as a key step for the asymmetric synthesis of various biologically active cyclopropanes Journal Article Organic Chemistry Frontiers 2018, 5, 409-414. @article{C7QO00737J, title = {Stereospecific C-H activation as a key step for the asymmetric synthesis of various biologically active cyclopropanes}, author = {S. Jerhaoui and P. Poutrel and J.-P. Djukic and J. Wencel-Delord and F. Colobert}, url = {http://dx.doi.org/10.1039/C7QO00737J}, doi = {10.1039/C7QO00737J}, year = {2018}, date = {2018-01-01}, journal = {Organic Chemistry Frontiers}, volume = {5}, pages = {409-414}, publisher = {The Royal Society of Chemistry}, keywords = {SYNCAT}, pubstate = {published}, tppubtype = {article} } |
| 60. | M. Mohankumar; M. Holler; E. Meichsner; J.-F. Nierengarten; F. Niess; J.-P. Sauvage; B. Delavaux-Nicot; E. Leoni; F. Monti; J. M. Malicka; M. Cocchi; E. Bandini; N. Armaroli Heteroleptic Copper(I) Pseudorotaxanes Incorporating Macrocyclic Phenanthroline Ligands of Different Sizes Journal Article Journal of the American Chemical Society 2018, 140, 2336-2347. @article{doi:10.1021/jacs.7b12671, title = {Heteroleptic Copper(I) Pseudorotaxanes Incorporating Macrocyclic Phenanthroline Ligands of Different Sizes}, author = {M. Mohankumar and M. Holler and E. Meichsner and J.-F. Nierengarten and F. Niess and J.-P. Sauvage and B. Delavaux-Nicot and E. Leoni and F. Monti and J. M. Malicka and M. Cocchi and E. Bandini and N. Armaroli}, url = {https://doi.org/10.1021/jacs.7b12671}, doi = {10.1021/jacs.7b12671}, year = {2018}, date = {2018-01-01}, journal = {Journal of the American Chemical Society}, volume = {140}, number = {6}, pages = {2336-2347}, note = {PMID: 29298047}, keywords = {CMM}, pubstate = {published}, tppubtype = {article} } |
| 59. | F.J Bauer; P. C Thomas; S. Y Fouchard; S. J M Neunlist A new classification algorithm based on mechanisms of action Journal Article Computational Toxicology 2018, 5, 8 - 15. @article{BAUER20188b, title = {A new classification algorithm based on mechanisms of action}, author = {F.J Bauer and P. C Thomas and S. Y Fouchard and S. J M Neunlist}, url = {http://www.sciencedirect.com/science/article/pii/S2468111317300567}, doi = {https://doi.org/10.1016/j.comtox.2017.11.001}, issn = {2468-1113}, year = {2018}, date = {2018-01-01}, journal = {Computational Toxicology}, volume = {5}, pages = {8 - 15}, keywords = {BSM, CRHI}, pubstate = {published}, tppubtype = {article} } |