A regio- and stereoselective 1,3-dipolar cycloaddition for the synthesis of novel spiro-pyrrolothiazolyloxindoles and their antitubercular evaluation
A regio- and stereoselective 1,3-dipolar cycloaddition for the synthesis of novel spiro-pyrrolothiazolyloxindoles and their antitubercular evaluation
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DOI：
10.1016/j.ejmech.2010.09.019
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发表时间：
2010-12-01
影响因子：
6.7
通讯作者：
Sriram, Dharmarajan
中科院分区：
文献类型：
--
作者：
Prasanna, Pitchaimani;Balamurugan, Kamaraj;Sriram, Dharmarajan
由取代靛红和1，3-噻唑烷-4-羧酸衍生的甲亚胺叶立德与一系列2-（芳基亚甲基）-2，3-二氢-1H-茚-1-酮的1，3-偶极环加成反应，以中等产率区域和立体选择性地合成了29个新的螺吡咯并噻唑基吲哚酮.采用琼脂稀释法筛选这些化合物的体外抗结核分枝杆菌H37 Ry（MTB）活性。在筛选的29种化合物中，螺[5.3 ′]-5 ′-硝基羟吲哚-螺[6.3 ″ 1- 2，3-二氢-1H-茚-1 ″-酮-7-（2，3-二氯苯基）四氢-1H-吡咯并[1，2-c][1，3]噻唑是活性最高的化合物，其对MTB的MIC为2.8 μ M，分别是环丙沙星和乙胺丁醇的1.67和2.70倍。(C)2010年Elsevier Masson SAS。All rights reserved.
The 1,3-dipolar cycloaddition of azomethine ylides derived from substituted isatins and 1,3-thiazolane-4-carboxylic acid to a series of 2-(arylmethylene)-2,3-dihydro-1H-inden-1-ones afforded twenty nine novel spiro-pyrrolothiazolyloxindoles regio- and stereoselectively in moderate yields. These compounds were screened for their in vitro activity against Mycobacterium tuberculosis H37Ry (MTB) using agar dilution method. Among 29 compounds screened, spiro[5.3']-5'-nitrooxindole-spiro-[6.3"1-2,3-dihydro-1H-inden-1"-one-7-(2,3-dichlorophenyl)tetrahydro-1H-pyrrolo[1,2-c][1,3]thiazole, was found to be the most active compound with MIC of 2.8 mu M against MTB, being 1.67 and 2.70 times more active than ciprofloxacin and ethambutol respectively. (C) 2010 Elsevier Masson SAS. All rights reserved.