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.
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.
School of Chemical Sciences, Kannur University, Payyanur Campus, Edat PO 670327, Kannur, Kerala, India.
P Karuvalam
PK
Ranjith
P
P
Rajeesh
Karickal R
KR
Haridas
Nayak K
NK
Susanta
Tayur N Guru
TN
Row
R
R
Rishikesan
N Suchetha
NS
Kumari
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001231:Aspergillus flavus / Q000187:drug effects; D001562:Benzimidazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002176:Candida albicans / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D015195:Drug Design; D004926:Escherichia coli / Q000187:drug effects; D007711:Klebsiella pneumoniae / Q000187:drug effects; D008958:Models, Molecular; D015394:Molecular Structure; D009161:Mycobacterium / Q000187:drug effects; D012233:Rhizopus / Q000187:drug effects; D013211:Staphylococcus aureus / Q000187:drug effects; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
C587423:5-bromo-1-((phenyl)sulfonyl)-2-((4-nitrophenoxy)methyl)-1H-benzimidazole; C587422:6-bromo-1-((phenyl)sulfonyl)-2-((4-nitrophenoxy)methyl)-1H-benzimidazole; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D001562:Benzimidazoles
Antibacterial activity; Antifungal activity; Antimycobacterial; Benzimidazole; SAR; X-ray crystallography