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8 results on '"Gwendal Grelier"'

1. Antiviral Compounds from Codiaeum peltatum Targeted by a Multi-informative Molecular Networks Approach

Author

Gwendal Grelier, Jean-Claude Guillemot, Johan Neyts, Leen Delang, Cécile Apel, Marc Litaudon, Florent Olivon, David Touboul, Cécilia Eydoux, Simon Remy, Fanny Roussi, Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS), Université de Lorraine (UL), Architecture et fonction des macromolécules biologiques (AFMB), Institut National de la Recherche Agronomique (INRA)-Aix Marseille Université (AMU)-Centre National de la Recherche Scientifique (CNRS), Rega Institute for Medical Research, Catholic University of Leuven - Katholieke Universiteit Leuven (KU Leuven), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Centre National de la Recherche Scientifique (CNRS)-Aix Marseille Université (AMU)-Institut National de la Recherche Agronomique (INRA), Rega Institute for Medical Research [Leuven, België], and Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Prioritization, Magnetic Resonance Spectroscopy, Stereochemistry, Pharmaceutical Science, Virus Replication, Antiviral Agents, 01 natural sciences, Analytical Chemistry, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, Drug Discovery, Moiety, ComputingMilieux_MISCELLANEOUS, Pharmacology, 010405 organic chemistry, Chemistry, Organic Chemistry, Euphorbiaceae, Zika Virus, Nuclear magnetic resonance spectroscopy, Dengue Virus, Terpenoid, 0104 chemical sciences, [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry, 010404 medicinal & biomolecular chemistry, Molecular network, Complementary and alternative medicine, Viral replication, Molecular networking, Molecular Medicine, Codiaeum peltatum, [SDV.TOX.ECO]Life Sciences [q-bio]/Toxicology/Ecotoxicology, [SDE.BE]Environmental Sciences/Biodiversity and Ecology, [CHIM.OTHE]Chemical Sciences/Other, Chikungunya virus, [CHIM.CHEM]Chemical Sciences/Cheminformatics
Abstract

From a set of 292 Euphorbiaceae extracts, the use of a molecular networking (MN)-based prioritization approach highlighted three clusters (MN1-3) depicting ions from the bark extract of Codiaeum peltatum. Based on their putative antiviral potential and structural novelty, the MS-guided purification of compounds present in MN1 and MN2 afforded two new daphnane-type diterpenoid orthoesters (DDO), codiapeltines A (1) and B (2), the new actephilols B (3) and C (4), and four known 1,4-dioxane-fused phenanthrene dimers (5-8). The structures of the new compounds were elucidated by NMR spectroscopic data analysis, and the absolute configurations of compounds 1 and 2 were deduced by comparison of experimental and calculated ECD spectra. Codiapeltine B (2) is the first daphnane bearing a 9,11,13-orthoester moiety, establishing a new major structural class of DDO. Compounds 1-8 and four recently reported monoterpenyl quinolones (9-12) detected in MN3 were investigated for their selective activities against chikungunya virus replication and their antipolymerase activities against the NS5 proteins of dengue and zika viruses. Compounds 3-8 exhibited strong inhibitory activities on both dengue and zika NS5 in primary assays, but extensive biological analyses indicated that only actephilol B (3) displayed a specific interaction with the NS5 targets. ispartof: JOURNAL OF NATURAL PRODUCTS vol:82 issue:2 pages:330-340 ispartof: location:United States status: published

Published
2019

2. Palladium(II)-Catalyzed Diastereoselective 2,3-Trans C(sp3)–H Arylation of Glycosides

Author

Samir Messaoudi, Nicolas Probst, Mouâd Alami, Vincent Gandon, Slimane Dahaoui, Gwendal Grelier, Laboratoire de Pharmacognosie (BioCIS), Université Paris-Sud - Paris 11 (UP11)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Cristallographie, Résonance Magnétique et Modélisations (CRM2), Université de Lorraine (UL)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), Université Paris-Sud - Paris 11 (UP11)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Laboratoire de chimie moléculaire (LCM), and Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-École polytechnique (X)

Subjects
chemistry.chemical_classification, C glycosides, 010405 organic chemistry, Aryl, chemistry.chemical_element, Glycoside, General Chemistry, 010402 general chemistry, 01 natural sciences, Medicinal chemistry, Catalysis, 0104 chemical sciences, chemistry.chemical_compound, chemistry, Stereoselectivity, [CHIM.OTHE]Chemical Sciences/Other, ComputingMilieux_MISCELLANEOUS, Palladium
Abstract

We report herein the diastereoselective C(sp3)–H arylation of glycosides. A wide range of β- and α-glycosides proved able to selectively undergo Pd(II)-catalyzed coupling with diverse aryl iodides to assemble a large library of functionalized 3-arylglycosylamides. DFT calculations were performed to elucidate the unexpected trans stereoselectivity of this reaction.

Published
2018

3. Dirhodium(II)-Mediated Alkene Epoxidation with Iodine(III) Oxidants

Author

María Ivana Lapuh, Philippe Dauban, Ali Nasrallah, Fernando Javier Duran, Gwendal Grelier, and Benjamin Darses

Subjects
010405 organic chemistry, Chemistry, Nitrene, Organic Chemistry, chemistry.chemical_element, Alkene epoxidation, 010402 general chemistry, Iodine, 01 natural sciences, Medicinal chemistry, 0104 chemical sciences, Rhodium, Reagent, Oxidizing agent, Lewis acids and bases, Physical and Theoretical Chemistry
Abstract

Dirhodium(II) complexes and iodine(III) oxidants have found useful applications in synthetic nitrene chemistry. In this study, the combination of the dirhodium(II) complex Rh2(tpa)4 (tpa = triphenylacetate) with the iodine(III) oxidant PhI(OPiv)2 is shown to promote the epoxidation of alkenes in the presence of 2 equivalents of water. The reaction can be applied to diversely substituted alkenes and the corresponding epoxides are isolated with yields of up to 90 %. A possible mechanism involves the dirhodium(II) complex as a Lewis acid species that would tune the oxidizing character of the iodine(III) reagent.

Published
2018

4. Hypervalent organoiodine compounds: from reagents to valuable building blocks in synthesis

Author

Philippe Dauban, Gwendal Grelier, Benjamin Darses, Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Département de Chimie Moléculaire (DCM), and Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Grenoble Alpes [2016-2019] (UGA [2016-2019])

Subjects
oxidation, Review, 010402 general chemistry, 01 natural sciences, Coupling reaction, Catalysis, lcsh:QD241-441, chemistry.chemical_compound, lcsh:Organic chemistry, Atom economy, tandem reactions, lcsh:Science, Nucleophilic addition, atom-economy, [CHIM.ORGA]Chemical Sciences/Organic chemistry, 010405 organic chemistry, Aryl, couplings, Organic Chemistry, Hypervalent molecule, Combinatorial chemistry, 0104 chemical sciences, Chemistry, hypervalent iodine, chemistry, Reagent, lcsh:Q, Stoichiometry
Abstract

Most of the polyvalent organoiodine compounds derive from iodoarenes, which are released in stoichiometric amounts in any reaction mediated by λ3- or λ5-iodanes. In parallel to the development of solid-supported reagents or reactions catalytic in iodine, a third strategy has emerged to address this issue in terms of sustainability. The atom-economy of transformations involving stoichiometric amounts of λ3- or λ5-iodanes, thus, has been improved by designing tandem reactions that allows for incorporating the aryl motif into the products through a subsequent one-pot nucleophilic addition or catalytic coupling reaction. This review summarizes the main achievements reported in this area.

Published
2018

5. Catalytic Intramolecular C(sp3 )-H Amination of Carbamimidates

Author

Philippe Dauban, Gwendal Grelier, Benjamin Darses, Pascal Retailleau, and Romain Rey-Rodriguez

Subjects
010405 organic chemistry, Chemistry, Intramolecular force, Organic Chemistry, Physical and Theoretical Chemistry, 010402 general chemistry, 01 natural sciences, Medicinal chemistry, Amination, 0104 chemical sciences, Catalysis
Published
2017

6. The Multiple Facets of Iodine(III) Compounds in an Unprecedented Catalytic Auto-amination for Chiral Amine Synthesis

Author

Philippe Dauban, Amanda G. Jarvis, Gwendal Grelier, Benjamin Darses, Julien Buendia, Frédéric Taran, Institut de Chimie des Substances Naturelles (ICSN), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Département de Chimie Moléculaire (DCM), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Grenoble Alpes [2016-2019] (UGA [2016-2019]), Service de Chimie Bio-Organique et de Marquage (SCBM), Médicaments et Technologies pour la Santé (MTS), Université Paris-Saclay-Direction de Recherche Fondamentale (CEA) (DRF (CEA)), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE)-Université Paris-Saclay-Direction de Recherche Fondamentale (CEA) (DRF (CEA)), and Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE)

Subjects
[CHIM.ORGA]Chemical Sciences/Organic chemistry, 010405 organic chemistry, Aryl, Hypervalent molecule, chemistry.chemical_element, Homogeneous catalysis, General Chemistry, [CHIM.CATA]Chemical Sciences/Catalysis, General Medicine, Iodine, 010402 general chemistry, 01 natural sciences, Catalysis, 0104 chemical sciences, chemistry.chemical_compound, chemistry, Reagent, Organic chemistry, Moiety, Amination, ComputingMilieux_MISCELLANEOUS
Abstract

Iodine(III) reagents are used in catalytic one-pot reactions, first as both oxidants and substrates, then as cross-coupling partners, to afford chiral polyfunctionalized amines. The strategy relies on an initial catalytic auto C(sp(3) )-H amination of the iodine(III) oxidant, which delivers an amine-derived iodine(I) product that is subsequently used in palladium-catalyzed cross-couplings to afford a variety of useful building blocks with high yields and excellent stereoselectivities. This study demonstrates the concept of self-amination of the hypervalent iodine reagents, which increases the value of the aryl moiety.

Published
2016

7. Intermolecular Rhodium(II)-Catalyzed Allylic C(sp 3)-H Amination of Cyclic Enamides

Author

Grégory Jestin, Romain Rey-Rodriguez, Philippe Dauban, Pascal Retailleau, Vincent Gandon, Isabelle Gillaizeau, Gwendal Grelier, Benjamin Darses, Institut de Chimie Organique et Analytique (ICOA), Université d'Orléans (UO)-Centre National de la Recherche Scientifique (CNRS)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Institut de Chimie du CNRS (INC)-Institut National de la Santé et de la Recherche Médicale (INSERM), Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), Université Paris-Sud - Paris 11 (UP11)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université d'Orléans (UO)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Paris-Sud - Paris 11 (UP11)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Allylic rearrangement, heterocycles, 010405 organic chemistry, Stereochemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Nitrene, Intermolecular force, chemistry.chemical_element, General Chemistry, [CHIM.CATA]Chemical Sciences/Catalysis, enamides, 010402 general chemistry, 01 natural sciences, 0104 chemical sciences, 3. Good health, Catalysis, Rhodium, chemistry.chemical_compound, nitrenes, chemistry, allylic amination, Functional group, rhodium catalysis, Chemoselectivity, Amination
Abstract

International audience; The intermolecular rhodium(II)-catalyzed C(sp 3)-H amination of enamides gives access to new 4-aminopiperidine derivatives that are useful building blocks in medicinal chemistry. This efficient transformation proceeds at room temperature with complete regio- and chemoselectivity in favor of the allylic C(sp 3)-H bond, and has a broad functional group tolerance. In addition, the matched combination of the chiral complex Rh2(S-nta)4 [nta = (S)-N-1,8-naphthoylalanine] with an optically pure (S)-sulfonimidamide allows the isolation of allylic amines with excellent stereocontrol.

Published
2018

8. Reaction of Ynamides with Iminoiodinane-Derived Nitrenes: Formation of Oxazolones and Polyfunctionalized Oxazolidinones

Author

Gwendal Grelier, Benjamin Darses, Philippe Dauban, Romain Rey-Rodriguez, Isabelle Gillaizeau, Pascal Retailleau, Loïc Habert, Institut de Chimie Organique et Analytique (ICOA), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université d'Orléans (UO)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie des Substances Naturelles (ICSN), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Département de Chimie Moléculaire (DCM), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Grenoble Alpes [2016-2019] (UGA [2016-2019]), Université d'Orléans (UO)-Centre National de la Recherche Scientifique (CNRS)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Institut de Chimie du CNRS (INC)-Institut National de la Santé et de la Recherche Médicale (INSERM), and Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)

Subjects
010405 organic chemistry, Chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Nitrene, Organic Chemistry, [CHIM.CATA]Chemical Sciences/Catalysis, 010402 general chemistry, 01 natural sciences, Combinatorial chemistry, 0104 chemical sciences, Catalysis, Reagent, Organic chemistry, Stereoselectivity, Lewis acids and bases, Stoichiometry, ComputingMilieux_MISCELLANEOUS
Abstract

This article describes the reaction of ynamides with metallanitrenes generated in the presence of an iodine(III) oxidant. N-(Boc)-Ynamides are converted to oxazolones via a cyclization reaction. The reaction is mediated by a catalytic dirhodium-bound nitrene species that first behaves as a Lewis acid. The oxazolones can be converted in a one pot manner to functionalized oxazolidinones following a regio- and stereoselective oxyamination reaction with the same nitrene reagent generated in stoichiometric amounts.

Published
2017

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