title: 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.
authors.affiliation: Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Ankara University, Ankara, Turkey.
authors.forename: İlgar
authors.initials: İ
authors.lastname: Kerimov
authors.forename: Gülgün
authors.initials: G
authors.lastname: Ayhan-Kilcigil
authors.forename: Elçin Deniz
authors.initials: ED
authors.lastname: Özdamar
authors.forename: Benay
authors.initials: B
authors.lastname: Can-Eke
authors.forename: Tülay
authors.initials: T
authors.lastname: Çoban
authors.forename: Süheyla
authors.initials: S
authors.lastname: Özbey
authors.forename: Canan
authors.initials: C
authors.lastname: Kazak
mesh_terms: D000818:Animals; D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001562:Benzimidazoles / Q000737:chemistry*; D001713:Biphenyl Compounds / Q000737:chemistry; D018360:Crystallography, X-Ray; D019363:Cytochrome P-450 CYP1A1 / Q000378:metabolism; D015195:Drug Design; D005609:Free Radicals / Q000378:metabolism; D066298:In Vitro Techniques; D015227:Lipid Peroxidation / Q000187:drug effects*; D008297:Male; D008862:Microsomes, Liver / Q000187:drug effects / Q000201:enzymology / Q000378:metabolism; D008872:Microwaves; D015394:Molecular Structure; D010069:Oxadiazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010851:Picrates / Q000737:chemistry; D051381:Rats; D017208:Rats, Wistar; D013329:Structure-Activity Relationship
chemical_list: D000975:Antioxidants; D001562:Benzimidazoles; D001713:Biphenyl Compounds; D005609:Free Radicals; D010069:Oxadiazoles; D010851:Picrates; C004931:1,1-diphenyl-2-picrylhydrazyl; C031000:benzimidazole; D019363:Cytochrome P-450 CYP1A1