In vitro Assessment of the Lipid Peroxidation of
N,N’-Disubstituted Benzimidazole-2-Thiones:
Hydrazides vs Esters

 Jelena Lazarević¹, Jelena Zvezdanović², Neda Anastassova³, Anelia Ts. Mavrova⁴,
Denitsa Yancheva³, Andrija Šmelcerović¹

 

¹University of Niš, Faculty of Medicine, Department of Chemistry, Niš, Serbia
²University of Niš, Faculty of Technology, Leskovac, Serbia
³Institute of Organic Chemistry with Center of Phytochemistry, Bulgarian Academy of Sciences, Sofia, Bulgaria
⁴University of Chemical Technology and Metallurgy, Department of Organic Synthesis, Sofia, Bulgaria

 

 SUMMARY

 

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]-1,3-dihydro-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 μM), with the best lipid peroxidation inhibition values (IC₅₀) shown for compound 5 (64 ± 10 μM) and compound 6 (73 ± 29 μM).
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.

 Keywords: antioxidant activity, lipid peroxidation, N,N’-disubstituted benzimidazole-2-thiones

 

 

Corresponding author:

Jelena Lazarević

e-mail: jelena.lazarevic@medfak.ni.ac.rs