微波辅助、简便、区域选择性的 Friedländer 合成及 2,9-二芳基-2,3-二氢噻吩并[3,2-b]喹啉类化合物的抗结核活性评价。
A microwave-assisted, facile, regioselective Friedländer synthesis and antitubercular evaluation of 2,9-diaryl-2,3-dihydrothieno-[3,2-b]quinolines.
机构信息
Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625021, Tamil Nadu, India.
出版信息
Eur J Med Chem. 2010 Feb;45(2):682-8. doi: 10.1016/j.ejmech.2009.11.011. Epub 2009 Nov 14.
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.
一系列 2,9-二芳基-2,3-二氢噻吩并[3,2-b]喹啉通过 5-芳基二氢-3(2H)-噻吩酮和 2-氨基二苯甲酮在三氟乙酸存在下，在 100 摄氏度微波辐射下以良好的收率进行弗里德尔环化反应，区域选择性地合成。对 2,9-二芳基-2,3-二氢噻吩并[3,2-b]喹啉进行了体外抗结核分枝杆菌活性筛选，包括结核分枝杆菌 H37Rv（MTB）和多药耐药结核分枝杆菌（MDR-TB）。在筛选的 17 种化合物中，7-氯-2-(2,4-二氯苯基)-9-苯基-2,3-二氢噻吩并[3,2-b]喹啉和 7-氯-2-(3-硝基苯基)-9-苯基-2,3-二氢噻吩并[3,2-b]喹啉对 MTB 和 MDR-TB 的 MIC 值分别为 0.90 和 0.95 μM，显示出最大的活性。
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