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

…, K Bracht, PJ Bednarski, M Lalk, P Langer

Index: Bose, Gopal; Bracht, Karin; Bednarski, Patrick J.; Lalk, Michael; Langer, Peter Bioorganic and Medicinal Chemistry, 2006 , vol. 14, # 14 p. 4694 - 4703

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Citation Number: 17

Abstract

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 ...