(1R,3S)-6-(2-Chloro-ethyl)-2,2,5,7-tetramethyl-indan-1,3,4-triol | 125472-36-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (1R,3S)-6-(2-Chloro-ethyl)-2,2,5,7-tetramethyl-indan-1,3,4-triol
• CAS: 125472-36-8
• 化学式: C₁₅H₂₁ClO₃
• 分子量: 284.783
• InChiKey: VQSCRMIYYGGVGW-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  60.69
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  1,5-二羟基-2,2,5,7-四甲基螺[1H-茚-6,1'-环丙烷]-4-酮 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 (1R,3S)-6-(2-Chloro-ethyl)-2,2,5,7-tetramethyl-indan-1,3,4-triol 、 (1R,3R)-6-(2-chloroethyl)-2,2,5,7-tetramethyl-1,3-dihydroindene-1,3,4-triol
  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

• Cytotoxic Illudane Sesquiterpenes from the Fungus <i>Granulobasidium vellereum</i> (Ellis and Cragin) Jülich
  作者：Christina Nord、Audrius Menkis、Anders Broberg

  DOI：10.1021/acs.jnatprod.5b00500

  日期：2015.11.25

  Eight illudane sesquiterpenes were obtained from the wood-decomposing fungus Granulobasidium vellereum (Ellis and Cragin) Julich; among them were the enantiomers of the known compounds illudin M (1) and dihydroilludin M (4) and the diastereomers of illudin M (2) and illudin S (3), as well as two previously undescribed illudanes (5, 6). The cytotoxicity of compounds 14 and 6 was evaluated against two tumor cell lines (Huh7 and MT4), which showed that compounds 13 had potent cytotoxic activity, whereas compounds 4 and 6 had no or only moderate effects at concentrations up to 400 mu M. Surprisingly, both compounds 2 and 3 were about 10 times more potent than 1. When the chemical reactivity of 1 and 2 was tested, compound 2 was shown to have a substantially higher reaction rate when reacted both with 2 M HCl and with cysteine, indicating that the difference in cytotoxicity is probably due to chemical reactivity and not to enzymatic affinity.
• 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.