一种微波辅助的简便区域选择性费歇尔吲哚合成法及新型2-芳基-3,4-二氢-2H-噻吩并[3,2-b]吲哚的抗结核活性评价
A microwave-assisted facile regioselective Fischer indole synthesis and antitubercular evaluation of novel 2-aryl-3,4-dihydro-2H-thieno[3,2-b]indoles.
作者信息
Karthikeyan Subramanian Vedhanarayanan, Perumal Subbu, Shetty Krithika Arun, Yogeeswari Perumal, Sriram Dharmarajan
机构信息
Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai, India.
出版信息
Bioorg Med Chem Lett. 2009 Jun 1;19(11):3006-9. doi: 10.1016/j.bmcl.2009.04.029. Epub 2009 Apr 14.
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.
通过5-芳基二氢-3(2H)-噻吩酮与盐酸芳基肼的反应，区域选择性地合成了一系列新型的2-芳基-3,4-二氢-2H-噻吩并[3,2-b]吲哚，产率良好。发现该反应受微波辅助。对噻吩并[3,2-b]吲哚进行了抗结核分枝杆菌H37Rv（MTB）和耐多药结核分枝杆菌（MDR-TB）的体外活性评估。在筛选的22种化合物中，[2-(2,4-二氯苯基)-7-氟-3,4-二氢-2H-噻吩并[3,2-b]吲哚]（6t）被发现是最具活性的化合物，对MTB和MDR-TB的最低抑菌浓度为0.4μg/mL。
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