One-Pot Synthesis of Pyrimidinothiazolidinones and Their Anti-Inflammatory and Antimicrobial Studies

• Published in: Phosphorus, sulfur, and silicon and the related elements sulfur, and silicon and the related elements, 2010-03, Vol.185 (3), p.501-508
• Main Authors: Lingappa, B., Sujith, K. V., Adhikari, Adithya, Rai, N. Satheesha, Vijaynarayana, K., Kalluraya, Balakrishna
• Format: Article
• Language: English
• Subjects: 5-nitro-2-thiophenaldiacetate; Acetic acid; Anti-inflammatory and antimicrobial activity; Antimicrobial agents; Microbiology; multicomponent reaction; pyrimidinones
• ISSN: 1042-6507; 1563-5325
• DOI: 10.1080/10426500902839384

In the present investigation, we report a one-pot synthesis of the title compounds, 2-arylidene-5-(2,3,6-trimethyl-4-methoxyphenyl)-7-substituted-5H-pyrimidino-[2,3-b]thiazolidine-3-ones 6a-j and 2-(5-nitro-2-thienylidine)-5-(2,3,6-trimethyl-4-methoxyphenyl)-7-substituted-5H- pyrimidino-[2,3-b]thiazolidine-3-ones 7a-e. Thus, 6a-j and 7a-e were prepared in good yields by refluxing 4-(2,3,6-trimethyl-4-methoxyphenyl)-6-methyl/aryl-3,4-dihydropyrimidin-2-(1H)-thiones 5, monochloro acetic acid, and anhydrous sodium acetate with the appropriate aromatic aldehyde/5-nitro-2-thiophenediacetate in acetic acid/acetic anhydride medium. The structures of these new compounds were established on the basis of their analytical and spectral data. Some of the newly synthesized compounds were screened for their anti-inflammatory and antimicrobial activity. They show moderate anti-inflammatory activity, and some of them were found to be promising antibacterial and antifungal agents. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.