A regio- and stereoselective 1,3-dipolar cycloaddition for the synthesis of novel spiro-pyrrolothiazolyloxindoles and their antitubercular evaluation

被引：170

作者：

Prasanna, Pitchaimani ^{[1
]}

Balamurugan, Kamaraj ^{[1
]}

Perumal, Subbu ^{[1
]}

Yogeeswari, Perumal ^{[2
]}

Sriram, Dharmarajan ^{[2
]}

机构：

[1] Madurai Kamaraj Univ, Sch Chem, Dept Organ Chem, Madurai 625021, Tamil Nadu, India

[2] Birla Inst Technol & Sci Pilani, Pharm Grp, Med Chem & Antimycobacterial Res Lab, Hyderabad 500078, Andhra Pradesh, India

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2010年 / 45卷 / 12期

关键词：

Antitubercular activity; Mycobacterium tuberculosis; Azomethine ylide; 1,3-Dipolar cycloaddition; 2-(Arylmethylene)-2,3-dihydro-1H-inden-1-ones; Spiro-pyrrolothiazolyloxindoles; STRUCTURE-BASED DESIGN; MAMMALIAN-CELL CYCLE; ANTIMYCOBACTERIAL EVALUATION; REGIOSELECTIVE SYNTHESIS; UNCARIA-TOMENTOSA; FACILE SYNTHESIS; TANDEM PROTOCOL; NITRILE OXIDES; OXINDOLE; DISCOVERY;

D O I：

10.1016/j.ejmech.2010.09.019

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

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.

引用

页码：5653 / 5661

页数：9

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