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Synthesis and structure-activity relationship studies of benzimidazole-thioquinoline derivatives as α-glucosidase inhibitors. 2023
Sara Moghadam Farid, and
Milad Noori, and
Mohammad Nazari Montazer, and
Minoo Khalili Ghomi, and
Marjan Mollazadeh, and
Navid Dastyafteh, and
Cambyz Irajie, and
Kamiar Zomorodian, and
Seyedeh Sara Mirfazli, and
Somayeh Mojtabavi, and
Mohammad Ali Faramarzi, and
Bagher Larijani, and
Aida Iraji, and
Mohammad Mahdavi
Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran.
In this article, different s-substituted benzimidazole-thioquinoline derivatives were designed, synthesized, and evaluated for their possible α-glucosidase inhibitory activities. The most active compound in this series, 6j (X = 4-bromobenzyl) exhibited significant potency with an IC50 value of 28.0 ± 0.6 µM compared to acarbose as the positive control with an IC50 value of 750.0 µM. The kinetic study showed a competitive inhibition pattern against α-glucosidase for the 6j derivative. Also, the molecular dynamic simulations were performed to determine key interactions between compounds and the targeted enzyme. The in silico pharmacodynamics and ADMET properties were executed to illustrate the druggability of the novel derivatives. In general, it can be concluded that these derivatives can serve as promising leads to the design of potential α-glucosidase inhibitors.
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