Molecular geometry and biological activity of 2-(4-substituted-phenylimino)thiazolidin- 4-one compounds

IF 1.3 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Bulletin of the Chemical Society of Ethiopia Pub Date : 2023-06-30 DOI:10.4314/bcse.v37i5.18

A. El-Rayyes, Roaa T. Mogharbel, Mohamed H. Abdel-Rhman, Mohamed A. Ismail, E. Abdel‐Latif

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Abstract

ABSTRACT. A series of 2-(4-substituted-phenylimino)thiazolidin-4-one compounds was synthesized via heterocyclizing the corresponding N-aryl-2-chloroacetamides with ammonium thiocyanate. Their chemical structures were elucidated based on an extensive analysis of their spectroscopic data, including infrared, 1H NMR, 13C NMR, and mass analyses. The possible tautomeric forms of synthesized thiazolidine-4-ones were studied. The tautomerization equilibrium parameters, ΔH, ΔG, and Keq were calculated using the DFT/B3LYP methodology, where it has been indicated that the tautomeric form, phenylimino, is more favourable than the phenylamino form. The antibacterial and antioxidant properties of the synthesized thiazolidin-4-ones were investigated. 2-(Chlorophenyl-imino)thiazolidin-4-one displayed potent antibacterial activity against E. coli (88.46%) and S. aureus (91.66%), and highest percent of inhibition (81.8%, ABTS assay). KEY WORDS: N-aryl-2-chloroacetamides, Ammonium thiocyanate, 2-(Arylimino)thiazolidin-4-ones, Mulliken’s charges, Dipole moment, ABTS assay Bull. Chem. Soc. Ethiop. 2023, 37(5), 1275-1286. DOI: https://dx.doi.org/10.4314/bcse.v37i5.18

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2-(4-取代苯基氨基)噻唑烷- 4- 1化合物的分子几何结构和生物活性

摘要用硫氰酸铵对相应的n-芳基-2-氯乙酰胺进行杂环化，合成了一系列2-(4-取代-苯基)噻唑烷-4- 1化合物。它们的化学结构是基于对光谱数据的广泛分析，包括红外，1H NMR, 13C NMR和质量分析来阐明的。对合成的噻唑烷-4-酮可能的互变异构形式进行了研究。使用DFT/B3LYP方法计算了互变异构平衡参数ΔH， ΔG和Keq，其中已表明互变异构形式苯基氨基比苯胺形式更有利。研究了合成的噻唑烷-4-酮类化合物的抗菌和抗氧化性能。2-(Chlorophenyl-imino)噻唑烷-4-one对大肠杆菌(E. coli)和金黄色葡萄球菌(S. aureus)的抑菌活性分别为88.46%和91.66%，ABTS实验显示其抑菌率最高(81.8%)。关键词:n-芳基-2-氯乙酰胺，硫氰酸铵，2-(芳基)噻唑烷-4-酮，Mulliken电荷，偶极矩，ABTS测定化学。Soc。阿比西尼亚人。2023年,37 (5),1275 - 1286 . DOI: https://dx.doi.org/10.4314/bcse.v37i5.18

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来源期刊

Bulletin of the Chemical Society of Ethiopia 化学-化学综合

CiteScore

2.20

自引率

8.30%

发文量

113

审稿时长

6-12 weeks

期刊介绍： The Bulletin of the Chemical Society of Ethiopia (BCSE) is a triannual publication of the Chemical Society of Ethiopia. The BCSE is an open access and peer reviewed journal. The BCSE invites contributions in any field of basic and applied chemistry.