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Design and synthesis of positional isomers of 5 and 6-bromo-1-(phenyl)sulfonyl]-2-(4-nitrophenoxy)methyl]-1H-benzimida zoles as possible antimicrobial and antitubercular agents

Ranjith, Karuvalam P and Rajeesh, P and Haridas, Karickal R and Susanta, Nayak K and Row, Guru Tayur N and Rishikesan, R and Kumari, Suchetha N (2013) Design and synthesis of positional isomers of 5 and 6-bromo-1-(phenyl)sulfonyl]-2-(4-nitrophenoxy)methyl]-1H-benzimida zoles as possible antimicrobial and antitubercular agents. In: Bioorganic & Medicinal Chemistry Letters, 23 (18). pp. 5228-5234.

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Official URL: http://dx.doi.org/10.1016/j.bmcl.2013.06.072

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-benzim idazoles derivatives 7(a-j) and 8(a j) synthesized in good yields and characterized by H-1 NMR, C-13 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 coil 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.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to Elsevier Science.
Keywords: Benzimidazole; Antibacterial Activity; Antifungal Activity; Antimycobacterial; X-Ray Crystallography; SAR
Department/Centre: Division of Chemical Sciences > Solid State & Structural Chemistry Unit
Depositing User: Francis Jayakanth
Date Deposited: 29 Oct 2013 05:43
Last Modified: 29 Oct 2013 05:43
URI: http://eprints.iisc.ac.in/id/eprint/47474

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