Synthesis and antioxidant properties of some novel 5H-dibenz[b,f]azepine derivatives in different in vitro model systems.

A series of 5H-dibenz[b,f]azepine containing different aminophenols and substituted aminophenols were synthesized. 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) with 3-chloro propionyl chloride. Further base condensation with different aminophenols and substituted aminophenols to produce series of 5H-dibenz[b,f]azepine containing aminophenol and substituted aminophenol (2a-e). The structures of newly synthesized compounds were characterized by spectral and elemental analysis. Their antioxidant properties were evaluated by using several methods: scavenging effects on 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical, inhibition of lipid peroxidation using beta-carotene linoleate system, inhibition of human low-density lipoprotein (LDL) oxidation and reducing power. Butylated Hydroxy Anisole (BHA) and Ascorbic acid (AA) were used as the reference antioxidant compounds and also the comparative study with the synthesized compounds was done. Under our experimental conditions, Compound (2) showed negligible activity over all the antioxidant assays but 5H-dibenz[b,f]azepine containing different aminophenols and substituted aminophenols (2a-e) showed good antioxidant activities over all the methods and compounds containing substituted aminophenols 2e and 2d showed predominant antioxidant activities among the synthesized analogues. Copyright 2009 Elsevier Masson SAS. All rights reserved.