Synthesis, in vitro α-amylase activity and molecular docking study of benzoxazole derivatives

IF 2.218 Q2 Chemistry Chemical Data Collections Pub Date : 2024-03-19 DOI:10.1016/j.cdc.2024.101133

Hayat Ullah , Fazal Rahim , Imad Uddin , Misbah Ullah Khan , Fahad Khan , Amjad Hussain , Rafaqat Hussain , Shoaib Khan

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Abstract

In current study, an efficient and simple synthesis of phenyl-benzoxazoles derivatives (1–14) were carried out, upon cyclization of 2-aminophenol with substituted aldehyde. All synthesized derivatives were characterized through NMR and HREI-MS spectroscopic techniques. All derivatives showed from excellent to moderate inhibitory potential with IC₅₀ value ranging from 0.80 ± 0.09 to 19.30 ± 0.49 µM as compared to the reference drug acarbose (IC₅₀ = 1.70 ± 0.10 µM). Derivative 9 (IC₅₀ = 0.80 ± 0.09 µM) was the most potent while derivative 10 (IC₅₀ = 1.03 ± 0.03 µM) with stand second most potent one. Structural activity relationship (SAR) was carried out which mainly depend upon nature, position and number of the substituent/s on aryl ring. Molecular docking study was carried out to determine the binding interaction of the most potent derivatives in the active site/s of enzyme.

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苯并恶唑衍生物的合成、体外 α 淀粉酶活性和分子对接研究

在本研究中，通过 2-aminophenol 与取代醛的环化反应，高效而简单地合成了苯基苯并恶唑衍生物 (1-14)。通过 NMR 和 HREI-MS 光谱技术对所有合成的衍生物进行了表征。与参比药物阿卡波糖（IC50 = 1.70 ± 0.10 µM）相比，所有衍生物都显示出了极好到中等程度的抑制潜力，IC50 值从 0.80 ± 0.09 到 19.30 ± 0.49 µM。衍生物 9（IC50 = 0.80 ± 0.09 µM）的药效最强，而衍生物 10（IC50 = 1.03 ± 0.03 µM）的药效次之。结构活性关系（SAR）主要取决于芳基环上取代基的性质、位置和数量。进行了分子对接研究，以确定最有效衍生物在酶活性位点的结合相互作用。

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来源期刊

Chemical Data Collections Chemistry-Chemistry (all)

CiteScore

6.10

自引率

0.00%

发文量

169

审稿时长

24 days

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