New Efficient Eco‐Friendly Supported ...
Document type :
Article dans une revue scientifique
DOI :
Permalink :
Title :
New Efficient Eco‐Friendly Supported Catalysts for the Synthesis of Amides with Antioxidant and Anti‐Inflammatory Properties
Author(s) :
Dufrénoy, Pierrick [Auteur]
Université catholique de Lille [UCL]
Charlet, Rogatien [Auteur]
Faculté de Médecine Henri Warembourg - Université de Lille
Unité de Glycobiologie Structurale et Fonctionnelle (UGSF) - UMR 8576
Hechelski, Marie [Auteur]
Université catholique de Lille [UCL]
Daïch, Adam [Auteur]
Université Le Havre Normandie [ULH]
Waterlot, Christophe [Auteur]
Université catholique de Lille [UCL]
Laboratoire Génie Civil et géo-Environnement (LGCgE) - ULR 4515
Jawhara, Samir [Auteur]
Faculté de Médecine Henri Warembourg - Université de Lille
Ghinet, Alina [Auteur]
null
Université catholique de Lille [UCL]
Facteurs de risque et déterminants moléculaires des maladies liées au vieillissement (RID-AGE) - U1167
Université catholique de Lille [UCL]
Charlet, Rogatien [Auteur]
Faculté de Médecine Henri Warembourg - Université de Lille
Unité de Glycobiologie Structurale et Fonctionnelle (UGSF) - UMR 8576
Hechelski, Marie [Auteur]
Université catholique de Lille [UCL]
Daïch, Adam [Auteur]
Université Le Havre Normandie [ULH]
Waterlot, Christophe [Auteur]
Université catholique de Lille [UCL]
Laboratoire Génie Civil et géo-Environnement (LGCgE) - ULR 4515
Jawhara, Samir [Auteur]
Faculté de Médecine Henri Warembourg - Université de Lille
Ghinet, Alina [Auteur]
null
Université catholique de Lille [UCL]
Facteurs de risque et déterminants moléculaires des maladies liées au vieillissement (RID-AGE) - U1167
Journal title :
ChemMedChem
Abbreviated title :
ChemMedChem
Volume number :
15
Pages :
459-467
Publisher :
Wiley
Publication date :
2020-02-12
ISSN :
1860-7187
English keyword(s) :
Amides
antioxidants
Eco-catalysts
Green chemistry
Idrocilamide
antioxidants
Eco-catalysts
Green chemistry
Idrocilamide
HAL domain(s) :
Sciences du Vivant [q-bio]
English abstract : [en]
A new environmentally friendly approach for the synthesis of idrocilamide (1), a marketed myorelaxant and anti-inflammatory agent, is reported herein. The synthetic strategy involves a solvent-free aminolysis reaction ...
Show more >A new environmentally friendly approach for the synthesis of idrocilamide (1), a marketed myorelaxant and anti-inflammatory agent, is reported herein. The synthetic strategy involves a solvent-free aminolysis reaction catalyzed by zinc-containing species (ZnCl2, montmorillonite K10 (MK10) impregnated with ZnCl2 or eco-catalysts). The latter have been prepared from the aerial parts of Lolium perenne L. plants grown on contaminated soils from northern France without and with thermal activation at 120 °C and supported on MK10 (Ecocat1 and Ecocat2, respectively). The best aminolysis catalysts in the current study (ZnCl2 and Ecocat2) were selected for additional aminolyses. Compared to ZnCl2, Ecocat2 had the advantage of being reusable over five test runs and constituted a sustainable catalyst allowing a green route to idrocilamide. Synthesized derivatives 1–4, 6 and 9 were first evaluated for their effect on reactive oxygen species (ROS) generation from macrophages and displayed antioxidant properties by preventing ROS production. Next, the analysis of the effect of molecules 1–4, 6 and 9 on macrophage migration between epithelial cells to human opportunistic fungus Candida albicans indicated that molecules 2–4, 6 and 9 exert anti-inflammatory properties via reducing macrophage migration while the parent idrocilamide (1) did not show any significant effect. This work opens the way for the discovery of new analogues of idrocilamide with improved properties.Show less >
Show more >A new environmentally friendly approach for the synthesis of idrocilamide (1), a marketed myorelaxant and anti-inflammatory agent, is reported herein. The synthetic strategy involves a solvent-free aminolysis reaction catalyzed by zinc-containing species (ZnCl2, montmorillonite K10 (MK10) impregnated with ZnCl2 or eco-catalysts). The latter have been prepared from the aerial parts of Lolium perenne L. plants grown on contaminated soils from northern France without and with thermal activation at 120 °C and supported on MK10 (Ecocat1 and Ecocat2, respectively). The best aminolysis catalysts in the current study (ZnCl2 and Ecocat2) were selected for additional aminolyses. Compared to ZnCl2, Ecocat2 had the advantage of being reusable over five test runs and constituted a sustainable catalyst allowing a green route to idrocilamide. Synthesized derivatives 1–4, 6 and 9 were first evaluated for their effect on reactive oxygen species (ROS) generation from macrophages and displayed antioxidant properties by preventing ROS production. Next, the analysis of the effect of molecules 1–4, 6 and 9 on macrophage migration between epithelial cells to human opportunistic fungus Candida albicans indicated that molecules 2–4, 6 and 9 exert anti-inflammatory properties via reducing macrophage migration while the parent idrocilamide (1) did not show any significant effect. This work opens the way for the discovery of new analogues of idrocilamide with improved properties.Show less >
Language :
Anglais
Audience :
Internationale
Popular science :
Non
Administrative institution(s) :
Université de Lille
CNRS
CNRS
Research team(s) :
Glycobiology in fungal Pathogenesis and Clinical Applications
Submission date :
2021-07-05T08:50:14Z
2021-07-09T11:25:55Z
2021-07-09T11:25:55Z