Facile water promoted synthesis of 1,2,3-triazolyl dihydropyrimidine-2-thione hybrids – Highly potent antibacterial agents

• Published in: European journal of medicinal chemistry Vol. 58; pp. 464 - 469
• Main Authors: Sangaraiah, Nagarajan, Murugan, Sathishkumar, Poovan, Shanmugavelan, Raja, Ranganathan, Alagusundaram, Ponnuswamy, Ramakrishnan, Venkatesan, Vellasamy, Shanmugaiah
• Format: Journal Article
• Language: English
• Published: ISSY-LES-MOULINEAUX Elsevier Masson SAS 01.12.2012; Elsevier
• Subjects: 1,2,3-Triazole; Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - pharmacology; Antibacterial; Biological and medical sciences; Chemistry, Medicinal; Dose-Response Relationship, Drug; Ethanol - chemistry; Life Sciences & Biomedicine; Medical sciences; Microbial Sensitivity Tests; Miscellaneous; Molecular Structure; Pharmacology & Pharmacy; Pharmacology. Drug treatments; Pseudomonas aeruginosa - drug effects; Pyrimidines - chemical synthesis; Pyrimidines - chemistry; Pyrimidines - pharmacology; Salmonella typhi - drug effects; Science & Technology; Staphylococcus aureus - drug effects; Streptococcus pneumoniae - drug effects; Structure-Activity Relationship; Tetracycline; Thione; Triazoles - chemical synthesis; Triazoles - chemistry; Triazoles - pharmacology; Water - chemistry; Water promoted; Thione; 1,2,3-Triazole; Antibacterial; Water promoted; Tetracycline; STAPHYLOCOCCUS-AUREUS; IDENTIFICATION; EPIDEMIOLOGY; AMIDES
• ISSN: 0223-5234; 1768-3254
• DOI: 10.1016/j.ejmech.2012.10.029

An elegant and efficient synthesis of hitherto novel 1,2,3-triazolyl dihydropyrimidine-2-thione hybrids has been accomplished for the first time in a green solvent viz. water. The hybrid molecules exhibit significant antibacterial activity when screened against four human pathogens viz. Streptococcus pneumonia, Staphylococcus aureus, Pseudomonas aeruginosa and Salmonella typhi. In comparison to the commercially marketed tetracycline, some of them were equally potent and a few more potent. An elegant green synthesis of 1,2,3-triazolyl dihydropyrimidine-2-thione hybrids in water has been accomplished for the first time. Their antibacterial activities are comparable with that of tetracycline. [Display omitted] ► It deals with the synthesis and antibacterial screening of hybrid molecules. ► The synthetic protocol eradicates the limitations associated with organic solvents. ► It uses the green solvent viz. water and hence eco-friendly. ► It involves simple work-up procedure affording good to excellent yields. ► Three hybrid molecules synthesized are equally/more potent than tetracycline.