期刊
CURRENT ORGANIC CHEMISTRY
卷 25, 期 17, 页码 2037-2044出版社
BENTHAM SCIENCE PUBL LTD
DOI: 10.2174/1385272825666210809142341
关键词
One-pot; isothiocyanate; thiosemicarbazones; pyrazoles; molecular docking; antioxidant; antibacterial
资金
- Taif University Researchers Supporting Project, Taif University, Taif, Saudi Arabia [TURSP-2020/43]
This study aimed to establish a novel catalytic eco-friendly one-pot reaction for the synthesis of thiosemicarbazone and N-thiocarbamoyl pyrazole derivatives, utilizing a silica-supported zinc chloride catalyst. The synthesized compounds exhibited potential antioxidant activity and were predicted to target bacterial cell walls as an undecaprenyl pyrophosphate synthase (UppS) inhibitor through molecular docking. Compared to other reported catalysts, the silica-zinc chloride catalyst was considered to be a more environmentally friendly and recyclable option.
The study aimed at a novel catalytic eco-friendly one-pot reaction for the synthesis of some new thiosemicarbazone and N-thiocarbamoyl pyrazole derivatives. The prepared and characterized silica-supported zinc chloride (ZnCl2/SiO2) catalyst has been presented for promoting the one-pot reaction between isothiocyanates (1 mmol), hydrazine (1.2 mmol) and 1,3dicarbonyl (1 mmol) compounds under solvent-free conditions. The identification data explained that the thiosemicarbazones products were obtained in the case of using ethyl acetoacetate as an example of 1,3-dicarbonyl compounds and N-thiocarbamoyl pyrazole derivatives products were obtained in the case of using acetylacetone as an example of 1,3dicarbonyl compounds. The presented catalyst silica-zinc chloride has been considered an eco-friendly and recyclable catalyst compared to the other reported catalyst. The biological activity of the synthesized compounds targeting the bacterial cell wall was predicted by the molecular docking as an undecaprenyl pyrophosphate synthase (UppS) inhibitor. Antioxidant data revealed the compounds 2a, 3d, 3e, 3f, 3g, 3h, and 3j to be promising antioxidant agents compared to ascorbic acid as a reference molecule.
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