Design and One-Pot and Microwave-Assisted Synthesis of 2-Amino/5-Aryl-1,3,4-Oxadiazoles Bearing a Benzimidazole Moiety as Antioxidants

Abstract

In this study, two new series of 2-amino-1,3,4-oxadiazoles and 5-aryl-1,3,4-oxadiazoles carrying a benzimidazole moiety were synthesized. The antioxidant properties of these compounds were investigated in vitro by the determination of the microsomal NADPH-dependent inhibition of lipid peroxidation levels (LP), the microsomal ethoxyresorufin O-deethylase activity (EROD), and DPPH radical scavenger effects. Among the tested compounds, 2-[(2-(4- chlorophenyl)-1H-benzo[d]imidazole-1-yl)methyl]-5-(4-fluorophenyl)-1,3, 4-oxadiazole (9) was found to be the most active compound in all three in vitro systems. Two new series of 2-amino-1,3,4-oxadiazoles and 5-aryl-1,3,4- oxadiazoles carrying a benzimidazole moiety were synthesized and their antioxidant properties were investigated in vitro. 2-[(2-(4-Chlorophenyl)-1H- benzo[d]imidazole-1-yl)methyl]-5-(4-fluorophenyl)-1,3,4-oxadiazole (9) was found to be the most active compound in all three in vitro systems. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.