Benzimidazole derivatives as potent α-amylase inhibitors: synthesis, characterization and in vitro α-amylase inhibition

苯并咪唑衍生物作为强效α-淀粉酶抑制剂:合成、表征及体外α-淀粉酶抑制活性

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Abstract

AIM: This study aims to evaluate the α-amylase inhibitory potential of newly synthesized benzimidazole derivatives, assessing their viability as prospective antidiabetic agents. MATERIALS & METHODS: A series of 2-(4-(1H-benzo[d]imidazol-2-yl)piperidin-1-yl)-N-phenylacetamide derivatives (7a-7j) were synthesized via an efficient synthetic route. The structural elucidation of these compounds was accomplished using advanced spectroscopic techniques, including mass spectrometry, FT-IR, (1)H & (13)C NMR, and elemental analysis. The α-amylase inhibitory activity of the synthesized compounds was evaluated in vitro, with IC₅₀ values determined to quantify their efficacy. To gain insights into the molecular interactions, molecular docking studies were conducted, followed by extensive molecular dynamics (MD) simulations. RESULT & DISCUSSION: All synthesized derivatives exhibited varying degrees of α-amylase inhibitory activity, with IC₅₀ values ranging from 1.10 ± 0.05 to 12.50 ± 0.30 μM. Notably, compounds 7b, 7c, and 7i demonstrated superior inhibitory effects, with IC₅₀ values of 1.20 ± 0.05, 1.40 ± 0.10, and 1.10 ± 0.05 μM, respectively, surpassing the standard drug acarbose (IC₅₀ = 1.70 ± 0.10 μM). CONCLUSION: The synthesized benzimidazole derivatives, notably compounds 7b, 7c, and 7i, demonstrated potent α-amylase inhibitory activity, surpassing the standard drug acarbose. These findings highlight their potential as lead compounds for developing novel antidiabetic agents.

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