Synthesis and Antimicrobial Activities of Novel 2-[substituted-1H-pyrazol-4-yl] Benzothiazoles, Benzoxazoles, and Benzimidazoles
Abstract
In an endeavor to find a new class of antimicrobial agents, a series of novel substituted benzimidazole, benzoxazole, and benzothiazole derivatives 6 containing pyrazole moiety have been synthesized by reaction of 3-aryl-4-formyl pyrazole 4 with substituted phenylenediamine or o-aminophenol or o-aminothiophenol 5. Reaction of phenyl hydrazine or 2-hydrazinopyridine 1 with substituted acetophenones 2 gave the corresponding hydrazones 3, which on Vilsmeier–Haack reaction with POCl3–DMF gave substituted 3-aryl-4-formyl pyrazoles 4. All final compounds 6a, 6b, 6c, 6d, 6e, 6f, 6g, 6h, 6i, 6j, 6k were evaluated for in vitro antibacterial activities against Escherichia coli and Staphylococcus aureus strains and in vitro antifungal activity against Candida albicans and Aspergillus niger strains by using serial dilution method. The antimicrobial activities were expressed as the minimum inhibitory concentration in µg/mL. The compound containing benzimidazole and benzoxazole moiety gave better antibacterial and antifungal activities than benzothiazole compounds.
