Synthesis, Biological Evaluation, and in-Silico Molecular Docking Studies of Multifunctional Thiazolidine Derivatives

IF 2.4 3区 化学 Q2 CHEMISTRY, ORGANIC
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Abstract

Herein we report the synthesis and biological evaluation of a new series of thiazolidin-4-one derivatives. The C4 and C5 functionalized, 5-arylidene/alkylidene, 5-bromo, 5-pyridinium, and 4-arylimino analogs of thiazolidine-4-one were prepared efficiently using appropriate synthetic routes and characterized by IR, NMR and Mass spectrometry. Results of antimicrobial evaluation showed that compounds 4 and 8 had significant antibacterial activity comparable to that of the reference drug gentamicin. Compound 5a showed promising antifungal activity compared to amphotericin B as a reference drug. The antitumor activity revealed that compound 4 was the most active analog among the tested series with IC50 values of 28.4 and 12.6 µg/mL against both HCT-116 and HepG-2 cell lines, respectively, compared to standard drug doxorubicin. Results from the biological evaluation, in-silico molecular docking studies, and ADMET analyses confirmed that thiazolidin-4-one is a promising scaffold that can be used to design potential lead compounds for the antibacterial and antitumor agents.

多功能噻唑烷衍生物的合成、生物学评价和室内分子对接研究
在此,我们报告了一系列新的噻唑烷-4-酮衍生物的合成和生物学评价。我们采用适当的合成路线高效地制备了噻唑烷-4-酮的 C4 和 C5 官能化、5-芳基/亚烷基、5-溴、5-吡啶和 4-芳基亚氨基类似物,并利用红外光谱、核磁共振和质谱对其进行了表征。抗菌评价结果表明,化合物 4 和 8 具有显著的抗菌活性,与参考药物庆大霉素相当。与参考药物两性霉素 B 相比,化合物 5a 显示出良好的抗真菌活性。抗肿瘤活性显示,化合物 4 是测试系列中活性最高的类似物,与标准药物多柔比星相比,它对 HCT-116 和 HepG-2 细胞系的 IC50 值分别为 28.4 和 12.6 µg/mL。生物学评估、硅内分子对接研究和 ADMET 分析的结果证实,噻唑烷-4-酮是一种很有前景的支架,可用于设计抗菌和抗肿瘤药物的潜在先导化合物。
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来源期刊
Polycyclic Aromatic Compounds
Polycyclic Aromatic Compounds 化学-有机化学
CiteScore
3.70
自引率
20.80%
发文量
412
审稿时长
3 months
期刊介绍: The purpose of Polycyclic Aromatic Compounds is to provide an international and interdisciplinary forum for all aspects of research related to polycyclic aromatic compounds (PAC). Topics range from fundamental research in chemistry (including synthetic and theoretical chemistry) and physics (including astrophysics), as well as thermodynamics, spectroscopy, analytical methods, and biology to applied studies in environmental science, biochemistry, toxicology, and industry. Polycyclic Aromatic Compounds has an outstanding Editorial Board and offers a rapid and efficient peer review process, as well as a flexible open access policy.
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