Synthesis of novel 3-chloro-1-(5H-dibenz[b,f]azepine-5yl)propan-1-one derivatives with antioxidant activity

Abstract

A series of 3-chloro-1-(5H-dibenz[b,f]azepine-5yl)propan-1-one derivatives (2a–k) bearing different amino acids were synthesized by base condensation reaction. 3-Chloro-1-(5H-dibenz[b,f]azepine-5yl)propan-1-one(2) was obtained by N-acylation of 5H-dibenz[b,f]azepine (1). All the synthesized compounds were evaluated for their potential over antioxidant activities against inhibition of lipid peroxidation by β-carotene and linoleic acid assay and inhibition of human low-density lipoprotein (LDL) oxidation assay. Typically, compound 2 showed weak antioxidant activity, whereas coupling of different amino acids enhances the antioxidant activities based on the presence of different functional groups. Among the derivatives, compound 2d showed significant antioxidant activities followed by 2h, 2i, 2j and 2k.