Design, synthesis, antioxidant properties and mechanism of action of new N,N′-disubstituted benzimidazole-2-thione hydrazone derivatives

摘要: Abstract New series of N,N′-disubstituted benzimidazole-2-thione were synthesized by introduction hydrazone moiety in the side chains. The toxicological potential studied compounds was evaluated monitoring cell viability and levels lactate dehydrogenase, glutathione malonaldehyde isolated rat hepatocytes. antioxidant properties with lowest toxicity using oxidative stress induced tert-butylhydroperoxide (tert-BOOH) on unsubstituted benzimidazole-2-thiones containing methoxyphenyl moieties, which revealed cytotoxic effects hepatocytes, exhibited statistically significant cytoprotective similar to those quercetin. elucidation activity tested hydrazones complimented evaluation their protective effect against iron damage classic model systems basic biologically relevant molecules – lecithin deoxyribose. It demonstrated that all have Fe (II) cellular lipids. DFT calculations applied order calculate reaction enthalpies hydrogen atom abstraction single-electron transfer nonpolar polar medium estimate most probable mechanisms free-radicals scavenging comparison suggested for melatonin. membrane permeability characterized based calculated physico-chemical such as surface area, molecular weight, number rotatable bonds hydrogen-bond acceptors donors.