title: Identification of a novel series of N-phenyl-5-[(2-phenylbenzimidazol-1-yl)methyl]-1,3,4-oxadiazol-2-amines as potent antioxidants and radical scavengers.
abstract: In this study, some novel 5-[[2-(phenyl/p-chlorophenyl)-benzimidazol-1-yl]-methyl]-N-substituted phenyl-1,3,4-oxadiazol-2-amine derivatives (28-45) with an oxadiazole ring were synthesized. The antioxidant properties and radical scavenging activities of the compounds were investigated employing various in vitro systems: hepatic microsomal NADPH-dependent inhibition of lipid peroxidation levels, scavenging of DPPH free radicals, and inhibition of microsomal ethoxyresorufin O-deethylase activity (EROD). Compounds 34 and 41 were found to be good scavengers of DPPH radicals (76% and 84%) when compared to BHT (90%). Almost all of the compounds examined were found to possess a good inhibitor effect on the microsomal EROD activity. Moreover, 32 and 41 were more active analogs (97% and 98%) on the microsomal EROD activity than caffeine (85%).
authors.affiliation: Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Ankara University, Ankara, Turkey.
authors.forename: Gulgun
authors.initials: G
authors.lastname: Ayhan-Kilcigil
authors.forename: Canan
authors.initials: C
authors.lastname: Kuş
authors.forename: Tülay
authors.initials: T
authors.lastname: Çoban
authors.forename: Elcin D
authors.initials: ED
authors.lastname: Özdamar
authors.forename: Benay
authors.initials: B
authors.lastname: Can-Eke
mesh_terms: D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000818:Animals; D000975:Antioxidants / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D019363:Cytochrome P-450 CYP1A1 / Q000037:antagonists & inhibitors / Q000378:metabolism; D016166:Free Radical Scavengers / Q000737:chemistry / Q000494:pharmacology; D005609:Free Radicals / Q000378:metabolism; D015227:Lipid Peroxidation / Q000187:drug effects; D008297:Male; D008862:Microsomes, Liver / Q000187:drug effects / Q000378:metabolism; D010069:Oxadiazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D051381:Rats; D017208:Rats, Wistar; D013329:Structure-Activity Relationship
chemical_list: D000588:Amines; D000975:Antioxidants; D016166:Free Radical Scavengers; D005609:Free Radicals; D010069:Oxadiazoles; D019363:Cytochrome P-450 CYP1A1
keywords: Benzimidazoles; DPPH; EROD; Lipid peroxidation; Oxadiazoles