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Synthesis, In Vitro α-Amylase Activity, and Molecular Docking Study of New Benzimidazole Derivatives
Russian Journal of Organic Chemistry ( IF 0.8 ) Pub Date : 2021-07-18 , DOI: 10.1134/s1070428021060130
Hayat Ullah 1 , Hafeez Ullah 2 , F. Khan 2 , F. Rahim 2 , I. Uddin 2 , M. Taha 3 , M. Sarfraz 4 , S. A. Ali Shah 5, 6 , A. Aziz 7 , S. Mubeen 8
Affiliation  

Abstract

New benzimidazole derivatives were synthesized by reacting substituted phenacyl bromides with 1H-benzimidazole-2-thiols. The synthesized compounds were characterized through 1H and 13C NMR and high-resolution mass spectra. Their evaluation for α-amylase activity revealed inhibitory potential with IC50 values ranging from 1.20±0.05 to 19.10±0.30 μM against IC50 = 1.70±0.10 μM for the standard drug acarbose. Among the examined series, 2-[(1H-benzimidazole-2-yl)sulfanyl]-1-(3–nitrophenyl)ethan-1-one (IC50 = 1.20±0.05 µM) was the most potent. Other nitro-substituted analogs showed good potency with IC50 values of 2.10±0.10, 2.20±0.10 and 2.10±0.10 µM. Limited structure–activity relationship was established for all derivatives based on the nature, position, and number of substituents on the aryl ring. Binding sites of the most active compounds were determined by the molecular docking study.



中文翻译:

新苯并咪唑衍生物的合成、体外α-淀粉酶活性和分子对接研究

摘要

通过取代苯甲酰溴与 1 H-苯并咪唑-2-硫醇反应合成新的苯并咪唑衍生物。合成的化合物通过1 H 和13 C NMR 和高分辨率质谱进行了表征。他们对 α-淀粉酶活性的评估揭示了抑制潜力,IC 50值范围为 1.20±0.05 至 19.10±0.30 μM,而标准药物阿卡波糖的IC 50 = 1.70±0.10 μM。在检查的系列中,2-[(1 H -benzimidazole-2-yl)sulfanyl]-1-(3-nitrophenyl)ethan-1-one (IC 50 = 1.20±0.05 µM) 是最有效的。其他硝基取代的类似物显示出良好的 IC 50效力2.10±0.10、2.20±0.10 和 2.10±0.10 µM 的值。基于芳环上取代基的性质、位置和数量,所有衍生物都建立了有限的构效关系。最活性化合物的结合位点由分子对接研究确定。

更新日期:2021-07-19
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