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Synthesis and Biological Assessment of Benzimidazole-Acrylonitrile-1,2,3-Triazole Derivatives As Α-Glucosidase Inhibitors Publisher Pubmed



Hatamfayazi M1 ; Mahdavi M2 ; Moradi Dehaghi S1 ; Khoshneviszadeh M5 ; Iraji A3, 4
Authors

Source: Bioorganic Chemistry Published:2025


Abstract

In the pursuit of developing potent α-glucosidase inhibitors for managing diabetes, a series of novel benzimidazole-acrylonitrile-1,2,3-triazole derivatives were designed. Sixteen derivatives (12a-p) were synthesized by varying substituents on the phenyl ring of the N-phenylacetamide moiety. Among these, compound 12m emerged as highly effective against α-glucosidase, displaying an IC50 value of 6.0 ± 0.2 μM, significantly outperforming the positive control acarbose (IC50 = 752.0 ± 2.0 μM). The kinetic evaluation revealed that 12m acts as a reversible competitive inhibitor with a Ki value of 4.5 µM. Molecular modeling and dynamics simulations underscored favorable binding energies, highlighting interactions of these compounds with critical amino acids within the α-glucosidase active site. These findings position 12m as a promising candidate for the development of α-glucosidase inhibitors with potent anti-diabetic potential. © 2024 Elsevier Inc.
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