期刊
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
卷 197, 期 1, 页码 30-37出版社
TAYLOR & FRANCIS LTD
DOI: 10.1080/10426507.2021.1986504
关键词
Isothiocyanates; (1; 3-thiazolidin-2-ylidene) ketones; 7-thioxo[1; 3] thiazolo[3; 2-c]pyrimidines; cyclocondensation
资金
- National Academy of Science of Ukraine
A preparatively convenient method for the synthesis of new 7-thioxo[1,3]thiazolo[3,2-c]pyrimidine derivatives has been developed, showing potential antimicrobial and antioxidant activities that could have promising clinical applications.
A preparatively convenient one-pot method for the synthesis of new 7-thioxo[1,3]thiazolo[3,2-c]pyrimidine derivatives 3a-3l by the cyclocondensation of 5-methyl(1,3-thiazolidin-2-ylidene)ketones 1a-1c with aroyl 2a-2d and 2-thienyl 2e isothiocyanates for 6-10 h boiling in acetone has been developed. Studies of the antimicrobial and antioxidant activities potential of the obtained compounds revealed that [2-methyl-5-(4-nitrophenyl)-7-thioxo-2,3-dihydro-7H-[1,3]thiazolo[3,2-c]pyrimidine-8-yl](phenyl)methanone 3k, effect on the test culture of M. luteum at a concentration of 0.5% is close to the control drug vancomycin. Moreover, [5-(4-bromophenyl)-2-methyl-7-thioxo-2,3-dihydro-7H-[1,3]thiazolo[3,2-c]pyrimidin-8-yl](phenyl)methanone 3j has an antibacterial effect on the specified test culture at a minimum inhibitory concentration of 15.6 mu g/mL. In turn, 1-(2-methyl-5-(thiophen-2-yl)-7-thioxo-2,3-dihydro-7H-[1,3]thiazolo[3,2-c]pyrimidin-8-yl]ethanone 3d can be considered promising for further structural modification to enhance the antioxidant effect. The structure of all synthesized substances was established by spectral analysis (H-1 and C-13 NMR, LC-MS, and FT-IR). Additionally, the structure of compound 3i was confirmed by X-ray diffraction analysis.
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