Synthesis and antioxidant properties of novel N-methyl-1,3,4-thiadiazol-2-amine and 4-methyl-2H-1,2,4-triazole-3(4H)-thione derivatives of benzimidazole class

KUŞ C., KILCIGİL G., ÖZBEY S., KAYNAK F. B., Kaya M., Coban T., ...More

Bioorganic and Medicinal Chemistry, vol.16, no.8, pp.4294-4303, 2008 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 16 Issue: 8
  • Publication Date: 2008
  • Doi Number: 10.1016/j.bmc.2008.02.077
  • Journal Name: Bioorganic and Medicinal Chemistry
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.4294-4303
  • Keywords: N-methylthiosemicarbazides, N-methyltriazolylbenzimidazoles, N-methylthiadiazolyl-benzimidazoles, antioxidant, X-ray structure analysis, LIPID PEROXIDE FORMATION, MECHANISMS, INDOLE
  • Ankara University Affiliated: Yes

Abstract

Some novel 1-methyl-4-(2-(2-substitutedphenyl-1H-benzimidazol-1-yl)acetyl)thiosemicarbazides (16a-20a), 5-[(2-(substitutedphenyl)-1H-benzimidazol-1-yl)methyl]-N-methyl-1,3,4-thiadiazol-2-amines (17b-20b), and 5-[(2-(substitutedphenyl)-1H-benzimidazol-1-yl)methyl-4-methyl-2H-1,2,4-triazole-3(4H)-thiones (16c-20c) were synthesized and tested for antioxidant properties by using various in vitro systems. Compounds 16a-20a were found to be a good scavenger of DPPH radical (IC50, 26 μM; IC50, 30 μM; IC50, 43 μM; IC50, 55 μM; IC50, 74 μM, respectively) when compared to BHT (IC50, 54 μM). Noteworthy results could not be found on superoxide radical. Compound 19b, which is the most active derivative inhibited slightly lipid peroxidation (28%) at 10-3 M concentration. Compound 17c inhibited the microsomal ethoxyresorufin O-deethylase (EROD) activity with an IC50 = 4.5 × 10-4 M which is similarly better than the specific inhibitor caffeine IC50 = 5.2 × 10-4 M. © 2008 Elsevier Ltd. All rights reserved.