Synthesis of New Thiazole and Pyrazole Clubbed 1,2,3-Triazol Derivatives as Potential Antimycobacterial and Antibacterial Agents

• Published in: Polycyclic aromatic compounds 2022-07, Vol.42 (6), p.3216-3237
• Main Authors: Jagadale, Shivaji M., Abhale, Yogita K., Pawar, Hari R., Shinde, Abhijit, Bobade, Vivek D., Chavan, Abhijit P., Sarkar, Dhiman, Mhaske, Pravin C.
• Format: Article
• Language: English
• Subjects: 123-Triazole; Antibacterial activity; Antibacterial agents; Antimycobacterial activity; Bacterial diseases; Chemical synthesis; Cycloaddition; E coli; Pyrazole; Pyrazoles; Substitutes; Thiazole; Triazoles; Tuberculosis
• ISSN: 1040-6638; 1563-5333
• DOI: 10.1080/10406638.2020.1857272

New series of 4-methyl-2-(4-substituted phenyl)-5-(4-((4-(4-substituted phenyl)-1H-1,2,3-triazol-1-yl)methyl)-1-phenyl-1H-pyrazol-3-yl)thiazole, 6a-t and 4-(1,3-diphenyl-1H-pyrazol-4-yl)-1-((1,3-diphenyl-1H-pyrazol-4-yl)methyl)-1H-1,2,3-triazole, 11a-o derivatives have been synthesized by applying copper-catalyzed [3 + 2] cycloaddition reaction. The newly synthesized 1,3-thiazolyl-pyrazolyl-1,2,3-triazole (6a-t) and bis-pyrazolyl-1,2,3-triazole (11a-o) derivatives were screened for in vitro antimycobacterial activity against M. Tuberculosis H37Ra dormant and active and antibacterial activity against four pathogenic bacteria, E. coli (NCIM 2576), P. flurescence (NCIM 2059), S. aureus (NCIM 2602) and B. subtilis (NCIM 2162). Compounds 6a, 6f, 6j, 11e and 11m showed good activity against M tuberculosis H37Ra Active strain, also compounds 6g, 6h, 11f, 11n and 11o showed good activity against M tuberculosis H37Ra Dormant strain. Compounds 6b, 6i, 6l, 6o, 6r, 11k, 11l and 11m showed good activity against B. subtilis with IC 50 1.99-2.96 µg/mL. The antibacterial activity of thiazolyl-pyrazolyl-1,2,3-triazole and bis-pyrazolyl-1,2,3-triazole derivatives suggested that, these derivatives could lead to new compounds for treatment against bacterial infection.