Design, synthesis and biological evaluation of new series of benzotriazole-pyrazole clubbed thiazole hybrids as bioactive heterocycles: antibacterial, antifungal, antioxidant, cytotoxicity study

• Published in: Journal of molecular structure 2024-03, Vol.1299, p.136760, Article 136760
• Main Authors: Gangurde, Keshav B., More, Rahul A., Adole, Vishnu A., Ghotekar, Dattatray S.
• Format: Article
• Language: English
• Subjects: Antimicrobial; Antioxidant; Benzotriazole; Cytotoxicity; Pyrazole; Thiazole
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2023.136760

•A series of novel (E)-2-(2-((5-(1H-benzo[d][1,2,3]triazol-1-yl)-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene)hydrazinyl)-4-(aryl)thiazole derivatives have been synthesized via three component reaction.•The synthesized compounds have been screened for antibacterial activity against E. coli, B. subtilis, B. megaterium, and S. aureus and antifungal activity against A. niger, A. oryzae, Rhizophus spp., and C. albicans.•All thiazole derivatives exhibited potent antibacterial and antifungal action against all tested strains.•% Radical scavenging activity has been evaluated and results have shown good antioxidant potential of the synthesized compounds.•The cytotoxicity study has revealed that synthesized compounds have no to less toxicity. The need for novel heterocyclic compounds with robust biological action is a result of the emergence of numerous pandemics and microbial resistance. To search antibacterial and antifungal lead compounds, a series of novel (E)-2-(2-((5-(1H-benzo[d][1,2,3]triazol-1-yl)-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene)hydrazinyl)-4-(aryl)thiazole derivatives were synthesized via three component reaction between 5-(1H-benzo[d][1,2,3]triazol-1-yl)-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde, thiosemicabazide and various substituted phenacyl bromides. The newly synthesized benzotriazole-pyrazole clubbed thiazole hybrids were characterized by FT-IR, 1H NMR, 13C NMR and HRMS methods. The synthesized compounds were screened for antibacterial activity against E. coli, B. subtilis, B. megaterium, and S. aureus and antifungal activity against A. niger, A. oryzae, Rhizophus spp., and C. albicans. All thiazole derivatives exhibited potent antibacterial and antifungal action against all tested strains. Besides, % radical scavenging activity was also evaluated and results showed good antioxidant potential of the synthesized compounds. The cytotoxicity study revealed that synthesized compounds has no to less toxicity as compared to standard Triton X-100. [Display omitted]