2-(对苯基)苯并恶唑-5-胺新系列1,3 -噻唑烷-4- 1衍生物的无溶剂催化合成、生物活性及对接研究

IF 1.7 4区 化学 Q3 CHEMISTRY, ORGANIC
Hussein Kaka Ahmed Khudhur, Awaz Jamil Hussein
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引用次数: 0

摘要

在本研究中,利用一种简单的磷酸三乙基铵盐(磷酸二氢三乙基铵)(4)作为一种廉价、高效的一锅三组分无溶剂合成噻唑烷-4-酮衍生物,产率良好至优异。使用FT-IR、1H-NMR、13C-NMR、13C-NMR-DEPT-135和MS等技术进行结构鉴定。通过微孔板滴度稀释技术对革兰氏阳性菌(S.Aureus)、革兰氏阴性菌(P.Aeruginosa和E.Coli)的体外抗菌作用和抗真菌活性(C.Albicans)证实了新获得的化合物的高效生物活性。最后,对金黄色葡萄球菌D-丙氨酸丙氨酰载体蛋白连接酶(PDB ID:7VHV)的晶体结构进行了分子对接研究。本研究旨在合成一系列与苯并恶唑部分结合的噻唑烷-4-酮衍生物。离子液体辅助一锅无溶剂合成法用于合成新系列噻唑烷-4-酮衍生物(10a-e)。通过(IR、1H-NMR、13C-NMR、13C-NMR-DEPT-135和MS)技术对新合成的结构鉴定和生物评价,高效的一锅三组分无溶剂合成噻唑烷-4-酮衍生物,产率良好至优异。大多数合成的化合物显示出高的生物活性和抗真菌活性,分别符合对上述微生物和PDB(ID:7VHV)晶体结构的对接研究。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Catalytic One-pot Solvent Free Synthesis, Biological Activity, and Docking Study of New Series of 1, 3-thiazolidine-4-one Derivatives Derived from 2- (P-tolyl) Benzoxazol-5-amine.

Objective: In this study, a simple triethylammonium salt of phosphoric acid (triethylammonium dihydrogen phosphate) (4) in the liquid state was utilized as an inexpensive, efficient one-pot three components, solvent-free synthesis of thiazolidine-4-one derivatives, with good to excellent yields. Techniques such as FT-IR, 1H-NMR, 13C-NMR, 13C-NMR-DEPT-135, and MS. were used for the structural elucidation. The high biotic efficiency of the newly obtained compounds was confirmed by in vitro antimicrobial action against Gram-positive (S. Aureus), Gram-negative bacteria (P. Aeruginosa and E. Coli) and antifungal activity (C. Albicans) via microplate titer dilution technique. Finally, a molecular docking study was performed with a resolved crystal structure of S. Aureus D-alanine alanyl carrier protein ligase (PDB ID: 7VHV). This investigation aimed to synthesize a new series of thiazolidine-4-one derivatives combined with benzoxazole moiety.

Material and methods: Ionic liquid assistance one-pot solvent-free synthesis method used to synthesize a new series of thiazolidine-4-one derivative 10(a-e).

Results: Structural identification of new synthesis and biological evaluation via techniques of (IR, 1H-NMR, 13C-NMR, 13C-NMR-DEPT-135, and MS).

Conclusion: Ionic liquid is utilized as an inexpensive, efficient one-pot three-component solvent-free synthesis of thiazolidine-4-one derivatives with good to excellent yields. Most of the synthesized compounds showed high biological and anti-fungal activity, in line with the docking study against mentioned microorganism and crystal structure of PDB (ID: 7VHV), respectively.

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来源期刊
Current organic synthesis
Current organic synthesis 化学-有机化学
CiteScore
3.40
自引率
5.60%
发文量
86
审稿时长
6-12 weeks
期刊介绍: Current Organic Synthesis publishes in-depth reviews, original research articles and letter/short communications on all areas of synthetic organic chemistry i.e. asymmetric synthesis, organometallic chemistry, novel synthetic approaches to complex organic molecules, carbohydrates, polymers, protein chemistry, DNA chemistry, supramolecular chemistry, molecular recognition and new synthetic methods in organic chemistry. The frontier reviews provide the current state of knowledge in these fields and are written by experts who are internationally known for their eminent research contributions. The journal is essential reading to all synthetic organic chemists. Current Organic Synthesis should prove to be of great interest to synthetic chemists in academia and industry who wish to keep abreast with recent developments in key fields of organic synthesis.
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