通过纳米氧化锌催化微波法合成新型铬烯基膦酸盐:通过分子对接、ADMET 分析和 α 淀粉酶抑制作用探索潜在的抗糖尿病药物

IF 1.8 3区 化学 Q3 CHEMISTRY, ORGANIC
Manjula Kavala , Raja Rajeswari Tiruveedula , Subramanyam Chennamsetty
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引用次数: 0

摘要

在无溶剂环境中,利用微波辐照,在纳米氧化锌催化下,通过迈克尔斯-阿尔布佐夫反应合成膦酸盐,开发出了一种更高效、更环保的方法。在合成之前,每个化合物都经过了硅学 ADMET 分析和分子对接,以评估其类似药物的特性及其抑制 α 淀粉酶的潜力。利用光谱分析验证了新合成化合物的结构,并评估了它们对α-淀粉酶的体外抑制作用。和 2-(1-甲基-1H-吲哚-3-基)-4-氧代-4H-苯并吡喃-6-基-6-膦酸二甲酯(6e)与参照物阿卡波糖相比显示出最高的抑制活性。此外,化合物 2-(苯并[d][1,3]二恶茂-4-基)-4-氧代-4H-苯并吡喃-6-基-6-膦酸二甲酯(6i)、4-氧代-2-苯基-4H-苯并吡喃-6-基-6-膦酸二甲酯(6a)和 2-(1H-苯并[d][1,3]二恶茂-4-基)-4-氧代-4H-苯并吡喃-6-基-6-膦酸二甲酯(6b和 2-(1H-吲哚-5-基)-4-氧代-4H-苯并吡喃-6-基-6-膦酸二甲酯(6g)与标准化合物相比,表现出几乎相同的有效抑制活性。其余化合物表现出中等到良好的酶抑制作用。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Synthesis of novel chromenyl phosphonates via nano-ZnO-catalyzed microwave method: Exploring potential anti-diabetic agents through molecular docking, ADMET analysis, and α-amylase inhibition

A more efficient and environmentally friendly approach has been developed for synthesizing phosphonates through the Michaelis-Arbuzov reaction, catalyzed by nano-ZnO in a solvent-free environment, utilizing microwave irradiation. Before synthesis, each compound underwent in silico ADMET analysis and molecular docking to assess drug-like characteristics and their potential to inhibit α-amylase. The structure of the newly synthesized compounds was validated using spectroscopic analysis, and their in vitro inhibitory effects on α-amylase were assessed. Among the compounds, dimethyl 2-(anthracen-10-yl)-4-oxo-4H-chromen-6-yl-6-phosphonate (6j), dimethyl 2-(naphthalen-1-yl)-4-oxo-4H-chromen-6-yl-6-phosphonate (6h), and dimethyl 2-(1-methyl-1H-indol-3-yl)-4-oxo-4H-chromen-6-yl-6-phosphonate (6e) displayed the highest inhibitory activity compared to the reference substance, acarbose. Additionally, compounds dimethyl 2-(benzo[d][1,3]dioxol-4-yl)-4-oxo-4H-chromen-6-yl-6-phosphonate (6i), dimethyl 4-oxo-2-phenyl-4H-chromen-6-yl-6-phosphonate (6a), and dimethyl 2-(1H-indol-5-yl)-4-oxo-4H-chromen-6-yl-6-phosphonate (6g) exhibited nearly equivalent effective inhibitory activity when compared to the standard. The remaining compounds demonstrated moderate to good enzyme inhibition.

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来源期刊
Synthetic Communications
Synthetic Communications 化学-有机化学
CiteScore
4.40
自引率
4.80%
发文量
156
审稿时长
4.3 months
期刊介绍: Synthetic Communications presents communications describing new methods, reagents, and other synthetic work pertaining to organic chemistry with sufficient experimental detail to permit reported reactions to be repeated by a chemist reasonably skilled in the art. In addition, the Journal features short, focused review articles discussing topics within its remit of synthetic organic chemistry.
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