Studies on quinones. Part 42: Synthesis of furylquinone and hydroquinones with antiproliferative activity against human tumor cell lines

被引：32
|
作者：
Benites, Julio [2 ]
Valderrama, Jaime A. [1 ]
Rivera, Felipe [1 ]
Rojo, Leonel [2 ]
Campos, Nair [3 ]
Pedro, Madalena [3 ]
Jose Nascimento, Maria Saeo [4 ]
机构：
[1] Pontificia Univ Catolica Chile, Fac Quim, Santiago, Chile
[2] Univ Arturo Prat, Dept Ciencias Quim & Farmaceut, Iquique, Chile
[3] Univ Porto, Fac Farm, Ctr Estudos Quim Organ Fitoquim & Farmacol, P-4100 Porto, Portugal
[4] Univ Porto, Fac Farm, Microbiol Lab, P-4100 Porto, Portugal
来源：
BIOORGANIC & MEDICINAL CHEMISTRY | 2008年 / 16卷 / 02期
关键词：
quinones; Michael addition; oxidative coupling; cytotoxicity;
D O I：
10.1016/j.bmc.2007.10.028
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
The preparation of furyl-1,4-quinone and hydroquinones by reaction of 2-furaldehyde N,N-dimethylhydrazone with benzo- and naphthoquinones is reported. Access to furylnaphthoquinones from unactivated quinones requires acid-induced conditions, however oxidative coupling reactions of activated quinones proceed under neutral conditions. The in vitro cytotoxic activity of the prepared compounds against a panel of three human cancer cell lines has been studied. Most of the furyl-1,4-quinones exhibited good antiproliferative activity (GI(50) = 6.5-33.5 mu m) against the MCF-7, NCI-H460, and SF-268 (CNS cancer) cell lines chosen for testing. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：862 / 868
页数：7
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