Synthesis of new 9-hydroxy-α- and 7-hydroxy-β-pyran naphthoquinones and cytotoxicity against cancer cell lines

被引：61

作者：

da Rocha, David R. ^{[1
]}

de Souza, Ana C. G. ^{[1
]}

Resende, Jackson A. L. C. ^{[2
]}

Santos, Wilson C. ^{[3
]}

dos Santos, Evelyne A. ^{[4
]}

Pessoa, Claudia ^{[4
]}

de Moraes, Manoel O. ^{[4
]}

Costa-Lotufo, Leticia V. ^{[4
]}

Montenegro, Raquel C. ^{[4
]}

Ferreira, Vitor F. ^{[1
]}

机构：

[1] Univ Fed Fluminense, Dept Quim Organ, BR-24020141 Rio De Janeiro, Brazil

[2] Univ Fed Fluminense, Dept Quim Inorgan, BR-24020141 Rio De Janeiro, Brazil

[3] Univ Fed Fluminense, Fac Farm, BR-24241000 Rio De Janeiro, Brazil

[4] Univ Fed Ceara, Expt Oncol Lab, Dept Fisiol & Farmacol, BR-60431970 Fortaleza, CE, Brazil

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2011年 / 9卷 / 11期

基金：

巴西圣保罗研究基金会;

关键词：

NOR-BETA-LAPACHONE; JUGLONE SERIES; APOPTOSIS; DERIVATIVES; INDUCTION; INHIBITION; EXPRESSION; SURVIVAL; REPAIR; DEATH;

D O I：

10.1039/c1ob05209h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthetic method to obtain alpha- and beta-pyran naphthoquinones 10 and 11 with a hydroxyl substituent on the aromatic ring was developed. Two series of alpha- and beta-pyran naphthoquinones were obtained from the 8-hydroxy-lawsone, and their anticancer properties were evaluated against four tumor cell lines. In general, the new compounds displayed good activity, possibly indicating that these compounds have increased pro-oxidant capacity. The 9-hydroxy-alpha-lapachone and 7-hydroxy-beta-lapachone analogues of the natural products alpha-lapachone and beta-lapachone were successfully produced by this methodology.

引用

页码：4315 / 4322

页数：8

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