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Synthesis and Antimicrobial Activities of Novel 2‐[substituted‐1 H ‐pyrazol‐4‐yl] Benzothiazoles, Benzoxazoles, and Benzimidazoles
Author(s) -
Padalkar Vikas S.,
Borse Bhushan N.,
Gupta Vinod D.,
Phatangare Kiran R.,
Patil Vikas S.,
Sekar Nagaian
Publication year - 2016
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.1506
Subject(s) - benzoxazole , benzothiazole , chemistry , benzimidazole , antimicrobial , moiety , pyrazole , aspergillus niger , aryl , candida albicans , minimum inhibitory concentration , combinatorial chemistry , hydrazine (antidepressant) , medicinal chemistry , stereochemistry , organic chemistry , microbiology and biotechnology , biochemistry , alkyl , biology
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 POCl 3 –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.