A microwave-assisted facile regioselective Fischer indole synthesis and antitubercular evaluation of novel 2-aryl-3,4-dihydro-2H-thieno[3,2-b]indoles.
A series of novel 2-aryl-3,4-dihydro-2H-thieno[3,2-b]indoles has been synthesised regioselectively in good yields from the reaction of 5-aryldihydro-3(2H)-thiophenones and arylhydrazine hydrochloride. This reaction is found to be assisted by microwaves. The thieno[3,2-b]indoles were evaluated for their in vitro activity against Mycobacterium tuberculosis H37Rv (MTB) and multi-drug resistant M. tuberculosis (MDR-TB). Among 22 compounds screened, [2-(2,4-dichlorophenyl)-7-fluoro-3,4-dihydro-2H-thieno[3,2-b]indole] (6t) was found to the most active compound with MIC of 0.4 microg/mL against MTB and MDR-TB.
Karthikeyan
Subramanian Vedhanarayanan
SV
Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai, India.
Perumal
Subbu
S
Shetty
Krithika Arun
KA
Yogeeswari
Perumal
P
Sriram
Dharmarajan
D
D000995:Antitubercular Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D024901:Drug Resistance, Multiple, Bacterial / Q000187:drug effects; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008872:Microwaves; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000995:Antitubercular Agents; D007211:Indoles