In vitro assessment of the lipid peroxidation of N,N'-disubstituted benzimidazole-2-thiones: Hydrazides vs esters

Abstract

Introduction: Oxidative stress and resulting lipid peroxidation are involved in numerous pathological conditions. For this reason, the role of antioxidants attracts attention and the radical-scavenging capacity of many natural and synthetic supplements and drugs has been extensively evaluated. Material and methods: In the present study, seven N,N'-disubstituted benzimidazole-2-thiones with ester (1 - 4) and hydrazide (5 - 7) side chains were investigated for in vitro antioxidant activity using lipid peroxidation method. Results: Among the assayed compounds, three hydrazides, 1,3-bis[3-(hydrazinooxy)-3-oxopropyl]-1,3dihydro-2H-benzimidazole-2-thione (5), 1,3-bis[3-(hydrazinooxy)-3-oxopropyl]-5-methyl-1,3-dihydro-2H benzimidazole-2-thione (6) and 1,3-bis[3-(hydrazinooxy)-3-oxopropyl]-5-benzoyl-1,3-dihydro-2H benzimidazole-2-thione (7) showed good antioxidant properties (IC50 ˂ 100 mM), with the best lipid peroxidation inhibition values (IC50) shown for compound 5 (64 ± 10 mM) and compound 6 (73 ± 29 mM). Conclusion: Indicated hydrazide structures may constitute a sort of molecular basis, a promising starting point for the development of compounds for the prevention and treatment of diseases resulting from oxidative damage.