A microwave-assisted, facile, regioselective Friedlander synthesis and antitubercular evaluation of 2,9-diaryl-2,3-dihydrothieno-[3,2-b]quinolines

作者：Balamurugan Kamaraj; Jeyachandran Veerappan; Perumal Subbu^*; Manjashetty Thimmappa H; Yogeeswari Perumal; Sriram Dharmarajan

来源：European Journal of Medicinal Chemistry, 2010, 45(2): 682-688.

DOI：10.1016/j.ejmech.2009.11.011

• Friedlander annulation
• Thienoquinoline
• 5-Aryldihydro-3(2H)-thiophenone
• 2-Aminobenzophenone
• Antimycobacterial activity
• Mycobacterium tuberculosis
• Multi-drug resistant Mycobacterium tuberculosis

A series of 2,9-diaryl-2,3-dihydrothieno[3,2-b]quinolines have been synthesized regioselectively by Friedlander 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-diatyl-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 mu M against MTB and MDR-TB respectively.

• 出版日期2010-2