Novel thiazole derivatives: Design, synthesis, antibacterial evaluation, DFT, molecular docking and in-silico ADMET investigations

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications Pub Date : 2025-01-02 DOI:10.1080/00397911.2024.2431989

Mohamed S. Mohamed Ahmed , Fawzy A. Attaby , Redhab A. J. Alfraiji , Zeinab A. Abdallah

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引用次数: 0

Abstract

Thiazole derivatives (7a-f and 9a-i) were synthesized in good yields (up to 98%). The synthetic protocol is achieved through a two-step reaction. The synthesized candidates were then evaluated for their antimicrobial efficacies against gram-positive and gram-negative bacteria. 4-methyl-2-(2-(3-(pentyloxy)benzylidene)hydrazinyl)-5-(p-tolyldiazenyl)thiazole showed significant antimicrobial activity against Staphylococcus aureus (ATCC: 13565) compared to ampicillin. On the other hand, 2-(2-(3-(hexyloxy)benzylidene)hydrazinyl)-4-(4-methoxyphenyl)thiazole shows potent activity against Klebsiella pneumonia (ATCC: 10031) compared to gentamicin as a standard antibiotic. The ADME profile of the prepared compounds indicated favorable pharmacological behaviors. Additionally, docking and in-silico ADMET analyses were performed for the promising derivatives and the results revealed strong antimicrobial activity. DFT calculations were performed, which provided additional insight into the thiazoles’ structure and formation.

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新型噻唑衍生物：设计、合成、抗菌评价、DFT、分子对接和硅ADMET研究

噻唑衍生物（7a-f和9a-i）的合成收率很高（可达98%）。合成方案是通过两步反应实现的。然后评估合成的候选物对革兰氏阳性和革兰氏阴性细菌的抗菌效果。与氨苄西林相比，4-甲基-2-（2-（3-（戊氧基）苄基）肼基）-5-（对氧基二氮基）噻唑对金黄色葡萄球菌的抑菌活性显著（ATCC: 13565）。另一方面，与庆大霉素相比，2-（2-（3-（己氧基）苄基）肼基）-4-（4-甲氧基苯基）噻唑作为标准抗生素对肺炎克雷伯菌具有较强的活性（ATCC: 10031）。制备的化合物的ADME谱显示了良好的药理行为。此外，对接和硅ADMET分析结果显示，这些有希望的衍生物具有很强的抗菌活性。进行了DFT计算，进一步了解了噻唑的结构和形成。

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来源期刊

Synthetic Communications 化学-有机化学

CiteScore

4.40

自引率

4.80%

发文量

156

审稿时长

4.3 months

期刊介绍： Synthetic Communications presents communications describing new methods, reagents, and other synthetic work pertaining to organic chemistry with sufficient experimental detail to permit reported reactions to be repeated by a chemist reasonably skilled in the art. In addition, the Journal features short, focused review articles discussing topics within its remit of synthetic organic chemistry.