新型噻唑啉酮衍生物:合成、生物学评价和硅学研究

IF 0.8 4区 化学 Q4 CHEMISTRY, ORGANIC Russian Journal of Organic Chemistry Pub Date : 2024-11-07 DOI:10.1134/S1070428024090136
W. O. Alsulami, Z. M. Al-Amshany, N. Y. Tashkandi, R. M. El-Shishtawy
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引用次数: 0

摘要

我们合成了一系列新型噻唑啉酮衍生物并对其进行了表征和生物活性研究。标题化合物是通过不同的醛 11a-11e 与硫代氨基甲酰肼缩合得到硫代氨基甲酰肼 12a-12e,这些化合物在乙酸钠存在下与溴乙酸乙酯环化得到新的噻唑啉酮衍生物 13a-13e。通过元素分析、傅立叶变换红外光谱和多核核磁共振(1H 和 13C)光谱,阐明了所有新合成化合物的结构。新合成的化合物 13a-13e 对细菌菌株大肠杆菌和金黄色葡萄球菌以及真菌菌株白色念珠菌表现出微弱或无抗菌活性。此外,还研究了 13a-13e 化合物的 ADME 特性,发现 13a 和 13b 衍生物符合 Lipinski 和 Veber 的规则,但 13c-13e 衍生物不符合这些规则。有希望的化合物 13a 和 13b 与表皮生长因子受体(EGFR)和血管内皮生长因子受体(VEGFR-2)的结合位点对接后,能量得分降低,拟合度提高,稳定性增强。
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Novel Thiazolinone Derivatives: Synthesis, Biological Evaluation, and In Silico Studies

A series of novel thiazolinone derivatives have been synthesized and characterized, and their biological activities have been studied. The title compounds were synthesized by condensation of different aldehydes 11a11e with thiosemicarbazide to give thiosemicarbazones 12a12e, which were cyclized with ethyl bromoacetate in the presence of sodium acetate to afford new thiazolinone derivatives 13a13e. The structure of all newly synthesized compounds was elucidated by elemental analysis and FTIR and multinuclear NMR (1H and 13C) spectroscopy. Newly synthesized compounds 13a13e showed weak or no antimicrobial activity against bacterial strains Escherichia coli and Staphylococcus aureus and fungal strain Candida albicans. Furthermore, the ADME properties of compounds 13a13e were examined, and derivatives 13a and 13b but not 13c13e were found to conform to Lipinskiʼs and Veberʼs rules without violations. The promising compounds 13a and 13b were docked against EGFR and VEGFR-2 binding sites with reduced energy scores, higher fitting, and stability.

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来源期刊
CiteScore
1.40
自引率
25.00%
发文量
139
审稿时长
3-6 weeks
期刊介绍: Russian Journal of Organic Chemistry is an international peer reviewed journal that covers all aspects of modern organic chemistry including organic synthesis, theoretical organic chemistry, structure and mechanism, and the application of organometallic compounds in organic synthesis.
期刊最新文献
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