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

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. © 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Citation

Pierrick Dufrénoy, Rogatien Charlet, Marie Hechelski, Adam Daïch, Christophe Waterlot, Samir Jawhara, Alina Ghinet. New Efficient Eco-Friendly Supported Catalysts for the Synthesis of Amides with Antioxidant and Anti-Inflammatory Properties. ChemMedChem. 2020 Mar 05;15(5):459-467

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PMID: 32022481

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