(S)-2-((3S,5S,8S,10S,13S,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,10,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)propanal | 1252023-86-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (S)-2-((3S,5S,8S,10S,13S,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,10,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)propanal
• CAS: 1252023-86-1
• 化学式: C₂₂H₃₄O₂
• 分子量: 330.511
• InChiKey: LOGVXQUTTMGKFX-PAOLRMKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.76
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (S)-2-((3S,5S,8S,10S,13S,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,10,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)propanal 、 溴化异戊基三苯基磷 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以47%的产率得到5α-cholesta-9(11),22-dien-3β-ol
  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：

  (3S,5S,8S,10S,13S,14S,17S)-10,13-dimethyl-17-((R)-2-methyloxiran-2-yl)-2,3,4,5,6,7,8,10,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol 在 三氟化硼乙醚 、 水 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以100%的产率得到(S)-2-((3S,5S,8S,10S,13S,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,10,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)propanal
  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