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.
Subject(s)
Antioxidants/chemical synthesis , Benzimidazoles/chemistry , Drug Design , Lipid Peroxidation/drug effects , Microwaves , Oxadiazoles/chemical synthesis , Animals , Antioxidants/chemistry , Antioxidants/pharmacology , Biphenyl Compounds/chemistry , Crystallography, X-Ray , Cytochrome P-450 CYP1A1/metabolism , Free Radicals/metabolism , In Vitro Techniques , Male , Microsomes, Liver/drug effects , Microsomes, Liver/enzymology , Microsomes, Liver/metabolism , Molecular Structure , Oxadiazoles/chemistry , Oxadiazoles/pharmacology , Picrates/chemistry , Rats , Rats, Wistar , Structure-Activity RelationshipABSTRACT
Some novel benzimidazole derivatives were synthesized and their in vitro effects on rat liver microsomal NADPH-dependent lipid peroxidation (LP) level, ethoxyresorufin O-deethylase (EROD) and antifungal activities were determined. A significant decrease in male rat liver microsomal LP level was noted by compounds 4c (52%), 4e (58%) and 4h (43%) at 10(-3) M concentration. Compounds 4c (100.0%), 4h (100.0%), 5c (98.0%) and 5h (100.0%) inhibited the microsomal ethoxyresorufin O-deethylase (EROD) enzyme activity better than that of the specific inhibitor caffeine (85%). Among these compounds, only compounds 4b and 4h exhibited moderate activity against C. albicans whereas the others had weak effects.
