Design, Synthesis and Antimicrobial Evaluation of New Arylazopyrazole and Arylazopyrazolo[1,5-a]pyrimidine Derivatives

Abstract

New series of arylazo-pyrazoles and arylazopyrazolo[1,5-a]pyrimidines are designed, synthesized, and evaluated for antimicrobial activity. The structures of new compounds were supported by IR, ¹H NMR, and MS spectral data. Our new synthesized compounds were screened for in vitro anti-bacterial and anti-fungal activities. It was found that most of the selected compounds exhibited antimicrobial activity especially compounds 3a, b, f which displayed excellent antibacterial and antifungal activities compared to the reference drugs Amikacin and Nystatin, respectively against the selected strains. Regarding antibacterial activity of the most potent compound, 3f; it elicited 1.6 folds Amikacin’s activity against B. subtilis and 0.8 of Amikacin activity against S. aureus, E. coli, and P. aeruginosa. Concerning the antifungal activity, 3f was 16 times and 4 times more potent than Nystatin against A. niger and C. albicans, respectively. Docking of 3f at the active site of MurA was studied to explore the mode of action of these compounds.

Graphical Abstract

Keywords:

• Antimicrobial activity
• docking
• pyrazole
• pyrazolo[1,5-a]pyrimidine
• synthesis