A microwave-assisted, facile, regioselective Friedländer synthesis and antitubercular evaluation of 2,9-diaryl-2,3-dihydrothieno-[3,2-b]quinolines.
A series of 2,9-diaryl-2,3-dihydrothieno[3,2-b]quinolines have been synthesized regioselectively by Friedländer annulation of 5-aryldihydro-3(2H)-thiophenones and 2-aminobenzophenones in the presence of trifluoroacetic acid in good yields under microwave irradiation at 100 degrees C. The 2,9-diaryl-2,3-dihydrothieno[3,2-b]quinolines were screened for in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv (MTB) and multi-drug resistant M. tuberculosis (MDR-TB). Among the 17 compounds screened, 7-chloro-2-(2,4-dichlorophenyl)-9-phenyl-2,3-dihydrothieno-[3,2-b]quinoline and 7-chloro-2-(3-nitrophenyl)-9-phenyl-2,3-dihydrothieno[3,2-b]quinoline display maximum activity with MIC of 0.90 and 0.95 muM against MTB and MDR-TB respectively.
Balamurugan
Kamaraj
K
Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625021, Tamil Nadu, India.
Jeyachandran
Veerappan
V
Perumal
Subbu
S
Manjashetty
Thimmappa H
TH
Yogeeswari
Perumal
P
Sriram
Dharmarajan
D
D000995:Antitubercular Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004353:Drug Evaluation, Preclinical; D024881:Drug Resistance, Bacterial; D008826:Microbial Sensitivity Tests; D008872:Microwaves; D008958:Models, Molecular; D008968:Molecular Conformation; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism; D013379:Substrate Specificity; D013696:Temperature
D000995:Antitubercular Agents; D011804:Quinolines; C037219:quinoline