Design, synthesis, antimicrobial activity and in silico molecular docking studies of some sulfur containing pyrazole-pyridine hybrids

IF 16.4 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Accounts of Chemical Research Pub Date : 2022-01-01 DOI:10.1080/10426507.2022.2085271

Nisheeth C. Desai , Dharmpalsinh J. Jadeja , Vijay M. Khedkar

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引用次数: 3

Abstract

We developed and synthesized novel 4-thiazolidinone hybrids with pyridine and pyrazole heterocycles (5a-5o). The structures of the synthesized products were elucidated by IR, ¹H NMR and ¹³C NMR spectroscopy and mass spectrometry. The synthesized hybrids were investigated for their antimicrobial activity against several bacterial and fungal strains using the Mueller–Hinton broth method. Compound 5-(3-methoxybenzylidene)-2-(1-phenyl-3-(p-tolyl)-1H-pyrazol-4-yl)-3-(pyridin-3-yl)thiazolidin-4-one (MIC = 50 μg/mL) exhibited prominent activity against gram-negative E. coli while compounds 5-(2-methylbenzylidene)-2-(1-phenyl-3-(p-tolyl)-1H-pyrazol-4-yl)-3-(pyridin-3-yl)thiazolidin-4-one and 5-(4-methylbenzylidene)-2-(1-phenyl-3-(p-tolyl)-1H-pyrazol-4-yl)-3-(pyridin-3-yl)thiazolidin-4-one exhibited MIC value of 250 μg/mL against C. albicans. Molecular docking study against microbial DNA gyrase could provide valuable insights into the binding modes of these molecules. They were found to exhibit excellent binding affinity (average Glide docking score: −7.989 and binding energy: −49.807 kcal/mol) through significant bonded and non-bonded interactions.

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含硫吡唑-吡啶杂化物的设计、合成、抑菌活性及硅内分子对接研究

我们开发并合成了新的4-噻唑烷酮杂环吡啶和吡唑杂环(5a- 50)。合成产物的结构通过IR、1H NMR、13C NMR和质谱分析进行了表征。采用Mueller-Hinton肉汤法研究了合成的杂交种对几种细菌和真菌的抗菌活性。(化合物5)- 3-methoxybenzylidene 2 - (1-phenyl-3 - (p-tolyl) 1 h-pyrazol-4-yl) 3 - (pyridin-3-yl) thiazolidin-4-one (MIC = 50μg / mL)对革兰氏阴性的大肠杆菌表现出突出的活动而化合物5 - (2-methylbenzylidene) 2 - (1-phenyl-3 - (p-tolyl) 1 h-pyrazol-4-yl) 3 - (pyridin-3-yl) thiazolidin-4-one和5 - (4-methylbenzylidene) 2 - (1-phenyl-3 - (p-tolyl) 1 h-pyrazol-4-yl) 3 - (pyridin-3-yl) thiazolidin-4-one展出MIC值为250μg / mL白念珠菌。对微生物DNA旋合酶的分子对接研究可以为深入了解这些分子的结合模式提供有价值的见解。通过显著的键和非键相互作用，发现它们具有良好的结合亲和力(平均Glide对接分数为−7.989，结合能为−49.807 kcal/mol)。

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来源期刊

Accounts of Chemical Research 化学-化学综合

CiteScore

31.40

自引率

1.10%

发文量

312

审稿时长

2 months

期刊介绍： Accounts of Chemical Research presents short, concise and critical articles offering easy-to-read overviews of basic research and applications in all areas of chemistry and biochemistry. These short reviews focus on research from the author’s own laboratory and are designed to teach the reader about a research project. In addition, Accounts of Chemical Research publishes commentaries that give an informed opinion on a current research problem. Special Issues online are devoted to a single topic of unusual activity and significance. Accounts of Chemical Research replaces the traditional article abstract with an article "Conspectus." These entries synopsize the research affording the reader a closer look at the content and significance of an article. Through this provision of a more detailed description of the article contents, the Conspectus enhances the article's discoverability by search engines and the exposure for the research.