6-(2-chloroethyl)-3,4-dihydroxy-2,2,5,7-tetramethyl-3H-inden-1-one | 144156-45-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 6-(2-chloroethyl)-3,4-dihydroxy-2,2,5,7-tetramethyl-3H-inden-1-one
• CAS: 144156-45-6
• 化学式: C₁₅H₁₉ClO₃
• 分子量: 282.767
• InChiKey: QKOFEJKMDZAHHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (6R)-6'-羟基-2',2',4',6'-四甲基-螺[环丙烷-1,5'-[5H]茚]-3',7'(2'H,6'H)-二酮 在 盐酸 作用下， 以 丙酮 为溶剂， 以56 mg的产率得到6-(2-chloroethyl)-3,4-dihydroxy-2,2,5,7-tetramethyl-3H-inden-1-one
  参考文献：
  名称：

  Structure-activity relationships of illudins: analogs with improved therapeutic index.

  摘要：

  Illudin S and M are extremely toxic sesquiterpenes produced by Omphalotus illudens. At low pH they behave as bifunctional alkylating agents, but at physiological pH they do not react with oxygen or nitrogen nucleophiles. Illudins react spontaneously with sulfur nucleophiles, glutathione or cysteine, at or slightly below pH 7, and toxicity to HL 60 cells can be modulated by altering glutathione levels in cells. Analogs of illudin M, e.g. the deoxy and, particularly, the dehydro derivatives, are less reactive to thiols and correspondingly less toxic to HL 60 cells than the parent compound. Dehydroilludin M has been found to be quite effective at inhibiting tumor growth in vivo at doses well tolerated by athymic nude mice.

  DOI：

  10.1021/jo00051a037

文献信息

• Structure-activity relationships of illudins: analogs with improved therapeutic index.
  作者：Trevor C. McMorris、Michael J. Kelner、Wen Wang、Leita A. Estes、Mark A. Montoya、Raymond Taetle

  DOI：10.1021/jo00051a037

  日期：1992.12

  Illudin S and M are extremely toxic sesquiterpenes produced by Omphalotus illudens. At low pH they behave as bifunctional alkylating agents, but at physiological pH they do not react with oxygen or nitrogen nucleophiles. Illudins react spontaneously with sulfur nucleophiles, glutathione or cysteine, at or slightly below pH 7, and toxicity to HL 60 cells can be modulated by altering glutathione levels in cells. Analogs of illudin M, e.g. the deoxy and, particularly, the dehydro derivatives, are less reactive to thiols and correspondingly less toxic to HL 60 cells than the parent compound. Dehydroilludin M has been found to be quite effective at inhibiting tumor growth in vivo at doses well tolerated by athymic nude mice.