Design, synthesis and biological evaluation of novel ketone derivatives containing benzimidazole and 1,3,4-triazole as CA inhibitors

ACAR ÇEVİK U., Isik A., Kapavarapu R., Kucukoglu K., NADAROĞLU H., BOSTANCI H. E., ...More

JOURNAL OF MOLECULAR STRUCTURE, vol.1295, 2024 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 1295
  • Publication Date: 2024
  • Doi Number: 10.1016/j.molstruc.2023.136770
  • Journal Name: JOURNAL OF MOLECULAR STRUCTURE
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, Chimica, Compendex, INSPEC
  • Anadolu University Affiliated: Yes

Abstract

In this study, we synthesized a series of new benzimidazole-triazole (6a-6k) derivatives and characterized them by 1H NMR, 13C NMR, and HRMS. These compounds were evaluated for their inhibitory activity against hCA-I and hCA-II. All the compounds exhibited good hCA-I and hCA-II inhibitory activities with IC50 values in the range of 1.158 mu M to 3.48 mu M. Among all these compounds, compound 6j, with an IC50 value of 1.288 mu M and 1.6197 mu M, is the most active against hCA-I and hCA-II, respectively. Compounds 6a-6k were also evaluated for their cytotoxic effects on the L929 mouse fibroblast (normal) cell line. Enzyme inhibition kinetics showed all compounds 6a-6k to inhibit the enzyme by non-competitive. The most active compound 6j was subjected to molecular docking, which revealed their binding interactions with the enzyme's active site, confirming the experimental findings.