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使用乙酸二异丙基乙基铵在室温下快速构建取代二氢噻吩脲甲酰胺:绿色视角

Rapid Construction of Substituted Dihydrothiophene Ureidoformamides at Room Temperature Using Diisopropyl Ethyl Ammonium Acetate: A Green Perspective.

作者信息

Jadhav Chetan K, Nipate Amol S, Chate Asha V, Dofe Vidya S, Sangshetti Jaiprakash N, Khedkar Vijay M, Gill Charansingh H

机构信息

Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad 431004, Maharashtra, India.

Department of Chemistry, Deogiri College of Science, Aurangabad 431005, Maharashtra, India.

出版信息

ACS Omega. 2020 Nov 5;5(45):29055-29067. doi: 10.1021/acsomega.0c03575. eCollection 2020 Nov 17.

Abstract

An economic, sustainable, and straightforward environmentally friendly synthesis of highly diversified polyfunctional dihydrothiophenes is successfully achieved via diisopropyl ethyl ammonium acetate as a room-temperature ionic liquid. Multicomponent synthesis contains domino processes; the benefit of this present protocol is highlighted by its readily available starting materials, superior functional group tolerance, purity of synthesized compounds was checked by high-performance liquid chromatography results in up to 99.7% purity for the synthesized compounds, reaction mass efficiency, effective mass yield, and excellent atom economy. In addition, a series of 2-(-carbamoyl acetamide)-substituted 2,3-dihydrothiophene analogs were synthesized, and selected samples were chosen for testing their in vitro antibacterial and antifungal activities. Furthermore, a molecular docking study against sterol 14α-demethylase could provide valuable insight into the mechanism of antifungal action providing an opportunity for structure-based lead optimization.

摘要

通过使用二异丙基乙铵乙酸盐作为室温离子液体,成功实现了一种经济、可持续且简单的环境友好型方法,用于高度多样化的多官能团二氢噻吩的合成。多组分合成包含多米诺过程;本方法的优势在于其起始原料易于获得、官能团耐受性优异,通过高效液相色谱法检查合成化合物的纯度,合成化合物的纯度高达99.7%,反应质量效率、有效质量产率和出色的原子经济性。此外,合成了一系列2-(-氨基甲酰基乙酰胺)取代的2,3-二氢噻吩类似物,并选择了部分样品测试其体外抗菌和抗真菌活性。此外,针对甾醇14α-脱甲基酶的分子对接研究可为抗真菌作用机制提供有价值的见解,为基于结构的先导化合物优化提供机会。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f330/7675536/d06a1af8dbf8/ao0c03575_0002.jpg

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