2-[(1S,5S)-5-[(1S,2S,4aS,6S,8aS)-1,6-diacetyloxy-8a-methyl-2,3,4,4a,5,6,7,8-octahydro-1H-naphthalen-2-yl]-2-acetyl-1-methylcyclopent-2-en-1-yl]ethyl acetate | 1252023-53-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-[(1S,5S)-5-[(1S,2S,4aS,6S,8aS)-1,6-diacetyloxy-8a-methyl-2,3,4,4a,5,6,7,8-octahydro-1H-naphthalen-2-yl]-2-acetyl-1-methylcyclopent-2-en-1-yl]ethyl acetate
• CAS: 1252023-53-2
• 化学式: C₂₇H₄₀O₇
• 分子量: 476.61
• InChiKey: MRCZYUMNBKEPEU-KZQTUTMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  96
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[(1S,5S)-5-[(1S,2S,4aS,6S,8aS)-1,6-diacetyloxy-8a-methyl-2,3,4,4a,5,6,7,8-octahydro-1H-naphthalen-2-yl]-2-acetyl-1-methylcyclopent-2-en-1-yl]ethyl acetate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以98%的产率得到
  参考文献：
  名称：

  Synthesis of cytotoxic novel 9,11-secosterol analogs: Structure/activity studies

  摘要：

  In an effort to determine the pharmaceutical utility and the structural requirements for activity against tumor cell lines, 30 novel 9,11-secosterol analogues with different side chains and degrees of oxidation at C-9 were synthesized starting from hecogenin. Evaluation of the synthesized compounds for cytotoxicity against KB, HeLa and MCF-7 cell lines revealed that some important structural features are required for activity. The presence of a cholesterol-type side chain, which appears to play a major role in determining the biological activity, the existence of a ketone functional at C-9 is also crucial for anticancer activity whereas hydroxyl/ketone function at C-22 on the side chain did not increase cytotoxicity. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2010.05.003
• 作为产物：
  描述：

  9,11-seco-5α-22-isoallospirosta-3β,9β,11-triol 、 乙酸酐 在 吡啶 、 氯化铵 、 chromium(VI) oxide 、 溶剂黄146 、 aluminum oxide 作用下， 以 水 、 1,2-二氯乙烷 、 苯 为溶剂， 反应 10.0h， 以49%的产率得到2-[(1S,5S)-5-[(1S,2S,4aS,6S,8aS)-1,6-diacetyloxy-8a-methyl-2,3,4,4a,5,6,7,8-octahydro-1H-naphthalen-2-yl]-2-acetyl-1-methylcyclopent-2-en-1-yl]ethyl acetate
  参考文献：
  名称：

  Synthesis of cytotoxic novel 9,11-secosterol analogs: Structure/activity studies

  摘要：

  In an effort to determine the pharmaceutical utility and the structural requirements for activity against tumor cell lines, 30 novel 9,11-secosterol analogues with different side chains and degrees of oxidation at C-9 were synthesized starting from hecogenin. Evaluation of the synthesized compounds for cytotoxicity against KB, HeLa and MCF-7 cell lines revealed that some important structural features are required for activity. The presence of a cholesterol-type side chain, which appears to play a major role in determining the biological activity, the existence of a ketone functional at C-9 is also crucial for anticancer activity whereas hydroxyl/ketone function at C-22 on the side chain did not increase cytotoxicity. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2010.05.003