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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
Authors:P. Karuvalam Ranjith  P. Rajeesh  Karickal R. Haridas  Nayak K. Susanta  Tayur N. Guru Row  R. Rishikesan  N. Suchetha Kumari
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
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(aj) and 8(aj) 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.
Keywords:Benzimidazole  Antibacterial activity  Antifungal activity  Antimycobacterial  X-ray crystallography  SAR
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