Design and synthesis of positional isomers of 5 and 6-bromo-1-[(phenyl)sulfonyl]-2-[(4-nitrophenoxy)methyl]-1H-benzimidazoles as possible antimicrobial and antitubercular agents |
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Authors: | P. Karuvalam Ranjith P. Rajeesh Karickal R. Haridas Nayak K. Susanta Tayur N. Guru Row R. Rishikesan N. Suchetha Kumari |
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Affiliation: | 1. School of Chemical Sciences, Kannur University, Payyanur Campus, Edat PO 670327, Kannur, Kerala, India;2. Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560012, India;3. Department of Chemistry, PG and Research Centre, Sri Paramakalyani College, Alwarkurichi, Tirunelveli 627412, Tamil Nadu, India;4. Department of Biochemistry, Justice K.S. Hegde Medical Academy, Deralakatte, India |
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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 1H NMR, 13C 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. |
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Keywords: | Benzimidazole Antibacterial activity Antifungal activity Antimycobacterial X-ray crystallography SAR |
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