SAR study of clubbed [1,2,4]-triazolyl with fluorobenzimidazoles as antimicrobial and antituberculosis agents

In the present study, a series of novel 2-[4-(1 H-[1,2,4]-triazol-1-yl)phenyl]-1-substituted-4,6-difluoro-1 H-benzo[ d]imidazole derivatives are synthesized by the alkylation of 2-[4-(1 H-[1,2,4]-triazol-1-yl)phenyl]-4,6-difluoro-1 H-benzo[ d]imidazole with substituted alkyl and aryl halides. The co...

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Bibliographic Details
Published in:European journal of medicinal chemistry 2009-07, Vol.44 (7), p.2930-2935
Main Authors: Jadhav, Ganesh Rajaram, Shaikh, Mohammad Usman, Kale, Rajesh Prabhakar, Shiradkar, Mahendra Ramesh, Gill, Charansingh Harnamsingh
Format: Article
Language:English
Subjects:
[1,2,4]-Triazole
Air oxidation
Alkylation
Anti-Infective Agents - chemical synthesis
Anti-Infective Agents - chemistry
Anti-Infective Agents - pharmacology
Antibacterial activity
Antibacterial agents
Antibiotics. Antiinfectious agents. Antiparasitic agents
Antimycobacterial
Antitubercular Agents - chemical synthesis
Antitubercular Agents - chemistry
Antitubercular Agents - pharmacology
Benzimidazoles - chemical synthesis
Benzimidazoles - chemistry
Benzimidazoles - pharmacology
Biological and medical sciences
Difluorobenzimidazole
General aspects
Medical sciences
Mycobacterium tuberculosis - drug effects
Pharmacology. Drug treatments
Structure-Activity Relationship
Triazoles - chemistry
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Summary:In the present study, a series of novel 2-[4-(1 H-[1,2,4]-triazol-1-yl)phenyl]-1-substituted-4,6-difluoro-1 H-benzo[ d]imidazole derivatives are synthesized by the alkylation of 2-[4-(1 H-[1,2,4]-triazol-1-yl)phenyl]-4,6-difluoro-1 H-benzo[ d]imidazole with substituted alkyl and aryl halides. The compounds were evaluated for their preliminary in-vitro antibacterial activity against Pseudomonas aeruginosa, Escherichia coli, Staphylococcus aureus, and Salmonella typhosa and then were screened for their antitubercular activity against Mycobacterium tuberculosis H37Rv strain by broth microdilution assay method. The antibacterial data suggested that the analogs with electronegative substituents emerged as promising antimicrobials. It was also observed that the promising antimicrobials have proved to be better antimycobacterials. Few of selected analogs are under further evaluation for secondary antitubercular screening, as they have shown better activity compared to rifampin. [Display omitted]
ISSN:0223-5234
1768-3254
DOI:10.1016/j.ejmech.2008.12.001