Synthesis and antidiabetic evaluation of benzimidazole‐tethered 1,2,3‐triazoles

• Published in: Archiv der Pharmazie (Weinheim) 2020-09, Vol.353 (9), p.e2000090-n/a
• Main Authors: Deswal, Laxmi, Verma, Vikas, Kumar, Devinder, Kaushik, Chander P., Kumar, Ashwani, Deswal, Yogesh, Punia, Suman
• Format: Article
• Language: English
• Subjects: 1,2,3‐triazole; antidiabetic; Antidiabetics; Antifungal agents; benzimidazole; docking; Fourier transforms; α‐amylase; α‐glucosidase
• ISSN: 0365-6233; 1521-4184
• DOI: 10.1002/ardp.202000090

Some novel benzimidazole‐tethered 1,2,3‐triazole derivatives (4a–r) were synthesized by a click reaction between 2‐substituted 1‐(prop‐2‐yn‐1‐yl)‐1H‐benzo[d]imidazole and in situ azide. The structures of the synthesized compounds were confirmed by spectroscopic studies (one‐ and two‐dimensional nuclear magnetic resonance, Fourier transform infrared, and high‐resolution mass spectra). The synthesized compounds were evaluated for their antidiabetic activity. Compounds 4a–r exhibited a good‐to‐moderate α‐amylase and α‐glucosidase inhibitory activity, with IC50 values ranging from 0.0410 to 0.0916 µmol/ml and 0.0146 to 0.0732 µmol/ml, respectively. Compounds 4e, 4g, and 4n were found to be most active. Furthermore, the binding conformation of the most active compounds was ascertained by docking studies. A series of new benzimidazole‐tethered 1,2,3‐triazole derivatives (4a–r) was synthesized by a click reaction between 2‐substituted 1‐(prop‐2‐yn‐1‐yl)‐1H‐benzo[d]imidazole and in situ azide. The evaluation of antidiabetic activity revealed that compounds 4a–r exhibited a good‐to‐moderate α‐amylase (IC50 = 0.0410–0.0916 µmol/ml) and α‐glucosidase inhibitory activity (IC50 = 0.0146–0.0732 µmol/ml). The binding conformation of the most active compounds (4e, 4g, and 4n) was ascertained by docking studies.