Novel three-component domino reactions of ketones, isatin and amino acids: Synthesis and discovery of antimycobacterial activity of highly functionalised novel dispiropyrrolidines

被引：137

作者：

Kumar, Raju Suresh ^{[1
]}

Rajesh, Stephen Michael ^{[1
]}

Perumal, Subbu ^{[1
]}

Banerjee, Debjani ^{[2
]}

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 / 01期

关键词：

Cascade reactions; Isatin; Sarcosine; Phenylglycine; Spiropyrrolidines; Anti-tubercular activity; N-MANNICH BASES; MULTICOMPONENT REACTIONS; BETA-THIOSEMICARBAZONES; SCHIZOPYRENUS-RUSSELLI; TUBERCULOSIS-CONTROL; CYSTICIDAL AGENTS; ANTIBACTERIAL; DERIVATIVES; ANTIFUNGAL; HETEROCYCLES;

D O I：

10.1016/j.ejmech.2009.09.044

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

One-pot three-component domino reactions of cyclic mono ketones, isatin and sarcosine/phenylglycine furnishing highly functionalised dispiropyrrolidines in moderate yields are described. The reaction when performed with cyclic amino acid, proline resulted in the dimerization of azomethine ylides. These compounds have been screened for their in vitro activity against Mycobacterium tuberculosis H37Rv (MTB) using agar dilution method. Among thirty eight compounds screened, 1-methyl-pyrrolo(spiro[2.3']-5-bromooxindole)spiro[3.2"]-1"- nitrosotetrahydro-4"(1H)-pyridinone (4t) was found to be the most active with MIC of 1.98 mu M against MTB and was 3.86 and 25.64 times more potent than the standard first line TB drugs, ethambutol and pyrazinamide respectively. (C) 2009 Elsevier Masson SAS. All rights reserved.

引用

页码：411 / 422

页数：12

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