Synthesis, reactions and structure-activity relationships of 1-hydroxyspiro[2.5]cyclooct-4-en-3-ones: Illudin analogs with in vitro cytotoxic activity

被引：21

作者：

Bose, Gopal

Bracht, Karin

Bednarski, Patrick J.

Lalk, Michael

Langer, Peter

机构：

[1] Univ Rostock, Inst Chem, D-18059 Rostock, Germany

[2] Univ Rostock, Leibniz Inst Katalyse eV, D-18059 Rostock, Germany

[3] Ernst Moritz Arndt Univ Greifswald, Inst Pharm, D-17487 Greifswald, Germany

[4] Ernst Moritz Arndt Univ Greifswald, Inst Chem & Biochem, D-17487 Greifswald, Germany

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2006年 / 14卷 / 14期

关键词：

cyclopropanes; cytotoxicity; illudins; spiro compounds; structure-activity relationship;

D O I：

10.1016/j.bmc.2006.03.037

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：

1-Hydroxyspiro [2.5]cyclooet-4-en-3-ones-analogs of natural illudines-were prepared in good yields by cyclization of 1,3-dicarbonyl dianions or 1,3-bis-silyl enol ethers ('masked dianions') with 1,1-diacylcyclopropanes. Several spirocyclopropanes showed a significant antiproliferative activity against human leukemia HL60 cells in vitro. 1-Hydroxyspiro [2.5]cyclooct-4-en-3-ones represent highly reactive precursors of unstable spiro[5.2]cycloocta-4,7-dien-6-ones and reactions with a number of nucleophiles were studied. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：4694 / 4703

页数：10

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