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Bioorg Med Chem Lett ; 23(18): 5228-34, 2013 Sep 15.
Article in English | MEDLINE | ID: mdl-23942420

ABSTRACT

In this Letter, we report the structure-activity relationship (SAR) studies on series of positional isomers of 5(6)-bromo-1-[(phenyl)sulfonyl]-2-[(4-nitrophenoxy)methyl]-1H-benzimidazoles derivatives 7(a-j) and 8(a-j) synthesized in good yields and characterized by (1)H NMR, (13)C NMR and mass spectral analyses. The crystal structure of 7a was evidenced by X-ray diffraction study. The newly synthesized compounds were evaluated for their in vitro antibacterial activity against Staphylococcus aureus, (Gram-positive), Escherichia coli and Klebsiella pneumoniae (Gram-negative), antifungal activity against Candida albicans, Aspergillus flavus and Rhizopus sp. and antitubercular activity against Mycobacterium tuberculosis H37Rv, Mycobacterium smegmatis, Mycobacterium fortuitum and MDR-TB strains. The synthesized compounds displayed interesting antimicrobial activity. The compounds 7b, 7e and 7h displayed significant activity against Mycobacterium tuberculosis H37Rv strain.


Subject(s)
Anti-Bacterial Agents/pharmacology , Antifungal Agents/pharmacology , Benzimidazoles/pharmacology , Drug Design , Anti-Bacterial Agents/chemical synthesis , Anti-Bacterial Agents/chemistry , Antifungal Agents/chemical synthesis , Antifungal Agents/chemistry , Aspergillus flavus/drug effects , Benzimidazoles/chemical synthesis , Benzimidazoles/chemistry , Candida albicans/drug effects , Dose-Response Relationship, Drug , Escherichia coli/drug effects , Klebsiella pneumoniae/drug effects , Models, Molecular , Molecular Structure , Mycobacterium/drug effects , Rhizopus/drug effects , Staphylococcus aureus/drug effects , Stereoisomerism , Structure-Activity Relationship
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