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

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 A^{3, 4}

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1. Faculty of Chemistry, Tehran North Branch, Islamic Azad University, Tehran, Iraq
2. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iraq
3. Stem Cells Technology Research Center, Shiraz University of Medical Sciences, Shiraz, Iraq
4. Department of Persian Medicine, School of Medicine, Research Center for Traditional Medicine and History of Medicine, Shiraz University of Medical Sciences, Shiraz, Iraq
5. Department of Medicinal Chemistry, Faculty of Pharmacy, Shiraz University of Medical Sciences, Shiraz, Iraq

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.

2. Rational Design of New Quinoline-Benzimidazole Scaffold Bearing Piperazine Acetamide Derivatives As Antidiabetic Agents, Bioorganic Chemistry (2024)

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Somayeh Mojtabavi (4)

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Style	Citing Format
MLA	Hatamfayazi M, et al.. "Synthesis and Biological Assessment of Benzimidazole-Acrylonitrile-1,2,3-Triazole Derivatives As Α-Glucosidase Inhibitors." Bioorganic Chemistry, vol. 154, no. , 2025, pp. -.
APA	Hatamfayazi M, Mahdavi M, Moradi Dehaghi S, Khoshneviszadeh M, Iraji A (2025). Synthesis and Biological Assessment of Benzimidazole-Acrylonitrile-1,2,3-Triazole Derivatives As Α-Glucosidase Inhibitors. Bioorganic Chemistry, 154(), -.
Chicago	Hatamfayazi M, Mahdavi M, Moradi Dehaghi S, Khoshneviszadeh M, Iraji A. "Synthesis and Biological Assessment of Benzimidazole-Acrylonitrile-1,2,3-Triazole Derivatives As Α-Glucosidase Inhibitors." Bioorganic Chemistry 154, no. (2025): -.
Harvard	Hatamfayazi M et al. (2025) 'Synthesis and Biological Assessment of Benzimidazole-Acrylonitrile-1,2,3-Triazole Derivatives As Α-Glucosidase Inhibitors', Bioorganic Chemistry, 154(), pp. -.
Vancouver	Hatamfayazi M, Mahdavi M, Moradi Dehaghi S, Khoshneviszadeh M, Iraji A. Synthesis and Biological Assessment of Benzimidazole-Acrylonitrile-1,2,3-Triazole Derivatives As Α-Glucosidase Inhibitors. Bioorganic Chemistry. 2025;154():-.
BibTex	@article{ author = {Hatamfayazi M and Mahdavi M and Moradi Dehaghi S and Khoshneviszadeh M and Iraji A}, title = {Synthesis and Biological Assessment of Benzimidazole-Acrylonitrile-1,2,3-Triazole Derivatives As Α-Glucosidase Inhibitors}, journal = {Bioorganic Chemistry}, volume = {154}, number = {}, pages = {-}, year = {2025} }
RIS	TY - JOUR AU - Hatamfayazi M AU - Mahdavi M AU - Moradi Dehaghi S AU - Khoshneviszadeh M AU - Iraji A TI - Synthesis and Biological Assessment of Benzimidazole-Acrylonitrile-1,2,3-Triazole Derivatives As Α-Glucosidase Inhibitors JO - Bioorganic Chemistry VL - 154 IS - SP - EP - PY - 2025 ER -

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