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New Efficient Eco‐Friendly Supported Catalysts for the Synthesis of Amides with Antioxidant and Anti‐Inflammatory Properties
Author(s) -
Dufrénoy Pierrick,
Charlet Rogatien,
Hechelski Marie,
Daïch Adam,
Waterlot Christophe,
Jawhara Samir,
Ghinet Alina
Publication year - 2020
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.201900641
Subject(s) - aminolysis , catalysis , chemistry , antioxidant , reactive oxygen species , environmentally friendly , zinc , combinatorial chemistry , organic chemistry , biochemistry , biology , ecology
Abstract 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.