1-羟基螺[2.5]环辛-4-烯-3-酮的合成、反应及构效关系：具有体外细胞毒性活性的隐杯伞素类似物
Synthesis, reactions and structure-activity relationships of 1-hydroxyspiro[2.5]cyclooct-4-en-3-ones: illudin analogs with in vitro cytotoxic activity.
作者信息
Bose Gopal, Bracht Karin, Bednarski Patrick J, Lalk Michael, Langer Peter
机构信息
Institut für Chemie und Biochemie, Universität Greifswald, Soldmannstr. 16, 17487 Greifswald, Germany.
出版信息
Bioorg Med Chem. 2006 Jul 15;14(14):4694-703. doi: 10.1016/j.bmc.2006.03.037. Epub 2006 Apr 17.
1-Hydroxyspiro[2.5]cyclooct-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.
1-羟基螺[2.5]环辛-4-烯-3-酮——天然伊鲁丁类似物——通过1,3-二羰基二阴离子或1,3-双硅烯醇醚（“掩蔽二阴离子”）与1,1-二酰基环丙烷环化反应以良好产率制备得到。几种螺环丙烷在体外对人白血病HL60细胞表现出显著的抗增殖活性。1-羟基螺[2.5]环辛-4-烯-3-酮是不稳定的螺[5.2]环辛-4,7-二烯-6-酮的高反应性前体，并对其与多种亲核试剂的反应进行了研究。
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