New Efficient Eco-Friendly Supported Catalysts for the Synthesis of Amides with Antioxidant and Anti-Inflammatory Properties.

Autor: Dufrénoy P; Laboratoire de chimie durable et santé, Yncréa Hauts-de-France, UCLille, 13 rue de Toul, 56046, Lille, France., Charlet R; Faculté de Médecine, Université de Lille, Place Verdun, 59045, Lille Cedex, France., Hechelski M; Institut Supérieur d'Agriculture, UCLille, 48 boulevard Vauban, 59046, Lille Cedex, France., Daïch A; UFR des Sciences et Techniques, Université Le Havre Normandie, 25 rue Philipe Lebon, 76063, Le Havre Cedex, France., Waterlot C; Institut Supérieur d'Agriculture, UCLille, 48 boulevard Vauban, 59046, Lille Cedex, France.; Institut Supérieur d'Agriculture, UCLille, 48 boulevard Vauban, 59046, Lille Cedex, France., Jawhara S; Faculté de Médecine, Université de Lille, Place Verdun, 59045, Lille Cedex, France., Ghinet A; Laboratoire de chimie durable et santé, Yncréa Hauts-de-France, UCLille, 13 rue de Toul, 56046, Lille, France.; Faculty of Chemistry, University of Iasi, Bd. Carol I, nr. 11, 700506, Iasi, Romania.
Jazyk: angličtina
Zdroj: ChemMedChem [ChemMedChem] 2020 Mar 05; Vol. 15 (5), pp. 459-467. Date of Electronic Publication: 2020 Feb 12.
DOI: 10.1002/cmdc.201900641
Abstrakt: 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 (ZnCl 2 , montmorillonite K10 (MK10) impregnated with ZnCl 2 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 (ZnCl 2 and Ecocat2) were selected for additional aminolyses. Compared to ZnCl 2 , 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.
(© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)
Databáze: MEDLINE
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