ChemMedChem
ChemMedChem
5 years ago

New efficient eco‐friendly supported catalysts for the synthesis of amides with antioxidant and anti‐inflammatory properties

Pierrick Dufrénoy, Rogatien Charlet, Marie Hechelski, Adam Daïch, Christophe Waterlot, Samir Jawhara, ALINA GHINET
New environment friendly approach for the synthesis of idrocilamide (1), the marketed myorelaxant and anti‐inflammatory agent, is reported. The synthetic strategy involves a solvent free aminolysis reaction catalyzed by different zinc‐containing catalysts: ZnCl2, montmorillonite K10 impregnated with ZnCl2 or ecocatalysts. The latter have been prepared from the aerial parts of Lolium perenne L. plants grown on contaminated soils from North of France region  The best aminolysis catalysts in the current study (ZnCl2 and Ecocat2) have been selected for additional aminolyses. Ecocat2 had the advantage of being reusable over five runs and constituted a sustainable catalyst allowing a green route to idrocilamide. Ecocat2 proved to be a versatile catalyst for amide bond formation via aminolysis of different methyl esters. Synthesized derivatives 1‐4, 6 and 9 have been first evaluated for their effect on reactive oxygen species (ROS) generation from macrophages and displayed antioxidant properties by preventing ROS generation. 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 parent idrocilamide (1) did not show any significant effect. This work opens the way for the discovery of new analogues of idrocilamide with improved antioxidant and anti‐inflammatory properties.

Publisher URL: https://onlinelibrary.wiley.com/doi/abs/10.1002/cmdc.201900641

DOI: 10.1002/cmdc.201900641

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