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Preparation, structural analysis, bioactivity assessment, enzyme and molecular docking calculations of some furan/thiophene-2-carboxamide derivatives
Journal of the Iranian Chemical Society ( IF 2.2 ) Pub Date : 2023-08-30 , DOI: 10.1007/s13738-023-02852-4
Sukriye Cakmak , Semiha Yenigun , Tevfik Ozen

Some furan/thiophene-2-carboxamide derivatives (1–3) were prepared from acyl chlorides and heterocyclic amine derivatives with good yields, employing synthetic route and their chemical structures were confirmed using different spectroscopic methods including IR, 1H NMR, 13C NMR and elemental analysis. Three different enzyme inhibition effect tests as urease, acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibiting activities, were applied to these compounds. The biological evaluation results clearly showed that the compound 1 showed approximately 9.8-fold more activity against urease enzyme than thiourea standard while the compound 3 showed approximately 4.2-fold more activity against BChE enzyme than galantamine standard. The molecular interaction for each of the target compounds with the active sites of the urease, acetylcholinesterase and butyrylcholinesterase enzymes was investigated by molecular insertion simulations and the results were confirmed the experimental findings. The results also show that compounds such as 1 and 3 carrying thiophene/furan carbocamide moieties could be used promising structures in the development of more potent pharmaceutical agents in the future.



中文翻译:

部分呋喃/噻吩-2-甲酰胺衍生物的制备、结构分析、生物活性评价、酶及分子对接计算

采用合成路线,以酰氯和杂环胺衍生物为原料,以良好的收率制备了一些呋喃/噻吩-2-甲酰胺衍生物( 1–3 ),并通过IR、 1 H NMR、13 C NMR等不同光谱方法确认了其化学结构和元素分析。对这些化合物进行了脲酶、乙酰胆碱酯酶(AChE)和丁酰胆碱酯酶(BChE)抑制活性三种不同的酶抑制效果测试。生物学评价结果清楚地表明,化合物1的抗脲酶活性是硫脲标准品的约9.8倍,而化合物3的抗脲酶活性是硫脲标准品的约9.8倍。对 BChE 酶的活性比加兰他敏标准品高约 4.2 倍。通过分子插入模拟研究了每种目标化合物与脲酶、乙酰胆碱酯酶和丁酰胆碱酯酶活性位点的分子相互作用,结果证实了实验结果。结果还表明,带有噻吩/呋喃碳酰胺部分的化合物(例如13)可以作为未来开发更有效药剂的有希望的结构。

更新日期:2023-08-30
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