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

Abstract

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.

Instigating the in vitro antidiabetic activity of new tridentate Schiff base ligand appended M(II) complexes: From synthesis, structural characterization, quantum computational calculations to molecular docking, and molecular dynamics simulation studies

“…The in vitro enzyme inhibition studies were performed using the protocol provided by Xiao et al and Deswal et al with minor modifications. [24][25][26]…”

Synthesis, Molecular Docking, and Bioactivity Study of Novel Hybrid Benzimidazole Urea Derivatives: A Promising α-Amylase and α-Glucosidase Inhibitor Candidate with Antioxidant Activity

“…Moreover, some benzimidazole structures having 5-bromo-2-arylbenzimidazole [ 41 ], conjugated biphenylbenzimidazole [ 42 ], benzimidazole linked with morpholine or piperazine [ 43 ], oxadiazole bearing benzimidazole motif [ 44 ], substituted arylbenzimidazol at para-position bridged with thiazolidinone [ 45 ], benzimidazole linked with Schiff base [ 46 ], benzimidazole bearing triazole [ 47 ], hybrid benzimidazole quinolinyl oxadiazole squeleton [ 48 ], hybrid benzimidazole with thiourea [ 49 ], and fluoro-2-substitued-1 H -benzimidazol substituted with morpholine [ 50 ] were reported as α-glucosidase inhibitors. In this context, benzimidazole derived from 5-oxo-pyrido triazepine and aminomethyloxo-pyrimido [ 51 ], benzoylaryl benzimidazole [ 52 ], benzimidazol with substituted benzylidene containing 2,4-thiazolidinedione, diethyl malonate, and methylacetoacetate [ 53 ], and benzimidazole bridged with triazole [ 54 ] also exhibited excellent α-amylase and α-glucosidase activities.…”

Design and synthesis of phenoxymethybenzoimidazole incorporating different aryl thiazole-triazole acetamide derivatives as α-glycosidase inhibitors

“…Benzimidazole-based compounds possess a wide range of pharmaceutical and biological activities, especially α-glycosidase inhibition [ 26 ]. Zawawi et al screened a novel series of thiourea derivatives bearing benzimidazole with IC 50 values between 35.83 and 297.99 μM which was better than the standard drug acarbose with IC 50 = 774.5 μM.…”