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12. Boron Compounds

Author

Kaufmann, D. E., additional, Matteson, D. S., additional, Chen, G., additional, Marder, T. B., additional, Nth, H., additional, Schilling, B., additional, Miyaura, N., additional, Hall, D. G., additional, Zheng, H., additional, Periasamy, M., additional, Seenivasaperumal, M., additional, Sivakumar, S., additional, Reddy, M. N., additional, Kumar, N. S., additional, Gennari, C., additional, Ceccarelli, S., additional, Piarulli, U., additional, Ishihara, K., additional, Yamamoto, H., additional, Habben, C., additional, Carboni, B., additional, Carreaux, F., additional, Gaumont, A. C., additional, Bakthan, Singaram, additional, Singaram, Bakthan, additional, Gabel, D., additional, El-Zaria, M. B., additional, cal, N., additional, Burmester, C., additional, Albrecht, K., additional, Vaultier, M., additional, Alcaraz, G., additional, Abu Ali, H., additional, Dembitsky, V. M., additional, Srebnik, M., additional, Murphy, P. J., additional, Zaidlewicz, M., additional, Meller, J., additional, Bubnov, Y., additional, Krzeminski, M., additional, Kster, M., additional, Teixidor, F., additional, and Vias, C., additional

Published
2005
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40. The Allyl Cyanate/Isocyanate Rearrangement: An Efficient Tool for the Stereocontrolled Formation of Allylic C–N Bonds

Author

Nocquet, P.-A., Henrion, S., Macé, A., Carboni, B., Villalgordo, J.M., Carreaux, F., Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Natural products, [CHIM]Chemical Sciences, Allylic compounds, Asymmetric synthesis, Rearrangement, Amines, Cyanates, Isocyanates
Abstract

International audience; [3,3]-Sigmatropic rearrangements represent powerful methods in the toolbox of synthetic organic chemists for the stereoselective construction of carbon–carbon as well as carbon–heteroatom bonds. Thus, the allyl cyanate/isocyanate rearrangement, although still underused for the preparation of allylamine derivatives, offers clear advantages over other similar methods. It usually occurs at or below ambient temperature with no need to use any metal catalyst, in a stereospecific way, and with a complete transfer of chirality. Moreover, combined with the high reactivity of the resulting isocyanates towards nucleophiles, this rearrangement gives access to various classes of compounds with wide structural and functional diversity. This microreview provides an overview of synthetic applications of this rearrangement since its discovery, with particular emphasis on its utility for the synthesis of complex nitrogen-containing molecules such as natural products. © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Published
2017
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41. 30th Franco-Belgian conference of Pharmacochemistry

Author

Aci-Seche, S. (Samia), Buron, F. (Frederic), Ple, K. (Karen), Robin, L. (Laurent), Suzenet, F. (Franck), Routier, S. (Sylvain), Bouyssou, P. (Pascal), Bazureau, J-P. (Jean-Pierre), Burgy, G. (Guillaume), Limanton, E. (Emmanuelle), Guiheneuf, S. (Solene), Carreaux, F. (Francois), Tahtouh, T. (Tania), Durieu, E. (Emilie), Meijer, L. (Laurent), Pipelier, M. (Muriel), Plenevaux, A. (Alain), Place, M. (Mattieu), Copin, C. (Chloe), Ambeu, C. (Christelle), Coulibaly Wacothon, K. (Karime), Paquin, L. (Ludovic), Mamyrbekova-Bekro Janat, A. (Akhanovna), Bekro, Y-A. (Yves-Alain), Benie, A. (Anoubile), Le Guevel, R. (Remy), Corlu, A. (Anne), Bach, S. (Stephane), Ruchaud, S. (Sandrine), Dago, C.D. (Camille Deliko), Brigaudeau, C. (Christophe), Mignen, O. (Olivier), Gally, J-M. (Jose-Manuel), Heinrich, J-T. (Jean-Thomas), Obled, A. (Alan), Bonnet, P. (Pascal), Gibault, F. (Floriane), Corvaisier, M. (Matthieu), Bailly, F. (Fabrice), Huet, G. (Guillemette), Cotelle, P. (Philippe), Duroux, R. (Romain), Renault, N. (Nicolas), Agouridas, L. (Laurence), Lopes, L. (Luisa), Melnyk, P. (Patricia), Yous, S. (Said), Piguel, S. (Sandrine), Stutzmann, A. (Aurelien), Schnetterle, M. (Marine), Caclard, A. (Arnaud), Biot, F. (Fabrice), Valade, E. (Eric), Bolla, J-M. (Jean-Michel), Pages, J-M. (Jean-Marie), Boyer, G. (Gerard), Alibert, S. (Sandrine), Neulat-Ripoll, F. (Fabienne), Elie, J. (Jonathan), Bidault, R. (Rudy), Arlicot, N. (Nicolas), Guilloteau, D. (Denis), Vercouille, J. (Johnny), D'attoma, J. (Joseph), Brun, P-L. (Pierre-Louis), Robin, Y. (Yves), Bostyn, S. (Stephane), Ejjoummany, A. (Abdelaziz), El Hakmaoui, A. (Ahmed), Guillaumet, G. (Gerald), Akssira, M. (Mohamed), Marx, S. (Sebastien), Dal Maso, T. (Thomas), Michiels, C. (Cerine), Wouters, J. (Johan), Prevost, J.R.C. (Julien R. C.), Van Ham, N.J.P. (Nicolas J. P.), Kozlova, A. (Arina), Frederick, R. (Raphael), Drapier, T. (Thomas), Geubelle, P. (Pierre), Bouckaert, C. (Charlotte), Goffin, E. (Eric), Dilly, S. (Sebastien), Hanson, J. (Julien), Pochet, L. (Lionel), Kastrup, J.S. (Jette Sandholm), Francotte, P. (Pierre), Pirotte, B. (Bernard), Champire, A. (Anthony), CHU Lille, Inserm, Université de Lille, Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS], Lille Neurosciences & Cognition (LilNCog) - U 1172, Lille Inflammation Research International Center - U 995 [LIRIC], and Centre de Recherche Jean-Pierre AUBERT Neurosciences et Cancer - U837 [JPArc]

Abstract

The “Journées Franco-Belges de Pharmacochimie” is a recognized annual meeting in organic and medicinal chemistry known for the quality of scientific exchange and conviviality. Young researchers were encouraged to present their work and share ideas with senior scientists. Abstracts of plenary lectures, oral communications, and posters presented during the meeting are collected in this report. 9;4

Published
2016

46. Synthesis and evaluation of new omega-borono-alpha-amino acids as rat liver arginase inhibitors

Author

Busnel, O., Carreaux, F., Carboni, B., Pethe, S., Goff, Sv, Mansuy, D., Boucher, Jl, and Deleage, Gilbert

Subjects
[SDV.BBM] Life Sciences [q-bio]/Biochemistry, Molecular Biology
Abstract

Recent studies have demonstrated that arginase plays important roles in pathologies such as asthma or erectile dysfunctions. We have synthesized new omega-borono-alpha-amino acids that are analogues of the previously known arginase inhibitors S-(2-boronoethyl)-l-cysteine (BEC) and 2-amino-6-boronohexanoic acid (ABH) and evaluated them as inhibitors of purified rat liver arginase (RLA). In addition to the distance between the B(OH)(2) and the alpha-amino acid functions, the position of the sulfur atom in the side chain also appears as a key determinant for the interaction with the active site of RLA. Furthermore, substitution of the alkyl side chain of BEC by methyl groups and conformational restriction of ABH by incorporation of its side chain in a phenyl ring led to inactive compounds. These results suggest that subtle interactions govern the affinity of inhibitors for the active site of RLA.Recent studies have demonstrated that arginase plays important roles in pathologies such as asthma or erectile dysfunctions. We have synthesized new omega-borono-alpha-amino acids that are analogues of the previously known arginase inhibitors S-(2-boronoethyl)-l-cysteine (BEC) and 2-amino-6-boronohexanoic acid (ABH) and evaluated them as inhibitors of purified rat liver arginase (RLA). In addition to the distance between the B(OH)(2) and the alpha-amino acid functions, the position of the sulfur atom in the side chain also appears as a key determinant for the interaction with the active site of RLA. Furthermore, substitution of the alkyl side chain of BEC by methyl groups and conformational restriction of ABH by incorporation of its side chain in a phenyl ring led to inactive compounds. These results suggest that subtle interactions govern the affinity of inhibitors for the active site of RLA.

Published
2005

47. Human DYRK2 in complex with Leucettine L41

Author

ELKINS, J.M., primary, SOUNDARARAJAN, M., additional, MUNIZ, J.R.C., additional, TAHTOUH, T., additional, BURGY, G., additional, DURIEU, E., additional, LOZACH, O., additional, COCHET, C., additional, SCHMID, R.S., additional, LO, D.C., additional, DELHOMMEL, F., additional, CARREAUX, F., additional, BAZUREAU, J.P., additional, MEIJER, L., additional, EDWARDS, A., additional, BOUNTRA, C., additional, and KNAPP, S., additional

Published
2012
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