H. B. Vasveliya, J. H. Pandya, H. K. Tilavat, A. J. Jivani
{"title":"One-Pot Biginelli Synthesis of New Pyrazole–Tetrahydropyrimidinethione Hybrids as Promising Antimycobacterial Agents","authors":"H. B. Vasveliya, J. H. Pandya, H. K. Tilavat, A. J. Jivani","doi":"10.1134/S1070428024604333","DOIUrl":null,"url":null,"abstract":"<p>Novel pyrazole–tetrahydropyrimidinethione hybrids were synthesized via a modified Biginelli reaction with a new 1,3-dicarbonyl compound derived from 1-methyl-1<i>H</i>-pyrazol-3-amine and ethyl acetoacetate. 6-Methyl-<i>N</i>-(1-methyl-1<i>H</i>-pyrazol-3-yl)-4-(substituted phenyl)-2-sulfanylidene-1,2,3,4-tetrahydropyrimidine-5-carboxamide derivatives were obtained in high yields using concentrated HCl as a catalyst. The products were characterized by NMR (<sup>1</sup>H and <sup>13</sup>C) spectroscopy and mass spectrometry and evaluated for their antitubercular activity against <i>M. tuberculosis</i> H37Rv. The 4-(trifluoromethyl)phenyl derivative showed the best activity (MIC = 3.12 μg/mL), while 4-fluorophenyl and 4-nitrophenyl analogues showed moderate efficacy (MIC = 6.25 and 12.5 μg/mL, respectively).</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 3","pages":"535 - 540"},"PeriodicalIF":0.8000,"publicationDate":"2025-05-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Russian Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1134/S1070428024604333","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Novel pyrazole–tetrahydropyrimidinethione hybrids were synthesized via a modified Biginelli reaction with a new 1,3-dicarbonyl compound derived from 1-methyl-1H-pyrazol-3-amine and ethyl acetoacetate. 6-Methyl-N-(1-methyl-1H-pyrazol-3-yl)-4-(substituted phenyl)-2-sulfanylidene-1,2,3,4-tetrahydropyrimidine-5-carboxamide derivatives were obtained in high yields using concentrated HCl as a catalyst. The products were characterized by NMR (1H and 13C) spectroscopy and mass spectrometry and evaluated for their antitubercular activity against M. tuberculosis H37Rv. The 4-(trifluoromethyl)phenyl derivative showed the best activity (MIC = 3.12 μg/mL), while 4-fluorophenyl and 4-nitrophenyl analogues showed moderate efficacy (MIC = 6.25 and 12.5 μg/mL, respectively).
期刊介绍：
Russian Journal of Organic Chemistry is an international peer reviewed journal that covers all aspects of modern organic chemistry including organic synthesis, theoretical organic chemistry, structure and mechanism, and the application of organometallic compounds in organic synthesis.
求助内容：
应助结果提醒方式：
京公网安备 11010802042870号
