Efficient synthesis of substituted 7-methyl-2H,5H-pyrano[4,3b]pyran-5-ones and evaluation of their in vitro antiproliferative/cytotoxic activities

被引：28

作者：

Leutbecher, Heiko

Williams, Lawrence A. D.

Roesner, Harald

Beifuss, Uwe

机构：

[1] Univ Hohenheim, Inst Chem, D-70599 Stuttgart, Germany

[2] Univ Hohenheim, Inst Zool, D-70599 Stuttgart, Germany

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2007年 / 17卷 / 04期

关键词：

heterocycles; Domino reaction; cytotoxicity; apoptosis; substituent effects;

D O I：

10.1016/j.bmcl.2006.11.045

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Substituted 7-methyl-2H,5H-pyrano[4,3-b]pyran-5-ones and related heterocycles 3 were synthesized through an efficient domino Knoevenagel condensation/6 pi-electron electrocyclization. In vitro antiproliferative/cytotoxic activity evaluation was performed with human SH-SY5Y neuroblastoma cells and revealed IC50 values ranging from 6.7 to > 200 mu M. The compound that was most cytotoxic to the neuroblastoma cells, that is, 2-isobutyl-3-isopropyl-7-methyl-2H,5H-pyrano[4,3-b]pyran-5-one (3a), also exhibited necrotic effects on the human IPC melanoma cells. (c) 2006 Elsevier Ltd. All rights reserved.

引用

收藏

页码：978 / 982

页数：5

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