Microwave-Assisted Synthesis and Antileishmanial Activity of 3-methoxycarbonyl-γ-butyrolactone Derivatives

被引：7

作者：

Pinatto-Botelho, Marcos F. ^{[1
]}

Crotti, Antonio E. M. ^{[1
]}

de Souza, Julia M. ^{[2
]}

Magalhaes, Lizandra G. ^{[2
]}

Donate, Paulo M. ^{[1
]}

机构：

[1] Univ Sao Paulo, Dept Quim, Fac Filosofia Ciencias & Letras Ribeirao Preto, BR-14040901 Ribeirao Preto, SP, Brazil

[2] Univ Franca, Nucleo Pesquisa Ciencias Exatas & Tecnol, BR-14404600 Franca, SP, Brazil

来源：

JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY | 2014年 / 25卷 / 08期

基金：

巴西圣保罗研究基金会;

关键词：

gamma-butyrolactone; multicomponent reaction; microwave-assisted synthesis; Leishmania amazonensis; METHYLENE-GAMMA-BUTYROLACTONES; ESSENTIAL OIL; SESQUITERPENE LACTONES; 15-DEOXYGOYAZENSOLIDE; CHEMISTRY;

D O I：

10.5935/0103-5053.20140113

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We describe the microwave-assisted synthesis of ten 3-methoxycarbonyl-gamma-butyrolactone derivatives and evaluate their in vitro antileishmanial activity against promastigote forms of Leishmania amazonensis. The synthesis furnished most of the compounds in 80-95% yield and reactions lasted about 10-20 min. Most of the compounds displayed IC50 values higher than 400 mu M. Compounds 5 (trans-3-(p-methoxy) benzyl-4-methyl-3-methoxycarbonyl-gamma-butyrolactone) and 10 (trans-3-(pmethoxy) benzyl-4-benzyl-3-methoxycarbonyl-gamma-butyrolactone) were the exceptions: they displayed IC50 values of 170.4 and 179.6 M, respectively, suggesting that the leishmanicidal activity of 3-methoxycarbonyl-gamma-butyrolactones may be related to the nature and size of the substituent at position C-4.

引用

页码：1331 / 1337

页数：7

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