(2aS,4S,6aS,8aS,8bR,9S,10R,11aS,12aS,12bS)-10-((S)-3-(1,3-dithiolan-2-yl)butyl)-6a,8a,9-trimethyl-1,2,2a,3,4,5,6,6a,8a,8b,9,10,11a,12,12a,12b-hexadecahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-8,2'-[1,3]dithiolan]-4-yl acetate | 1252023-65-6

• 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: (2aS,4S,6aS,8aS,8bR,9S,10R,11aS,12aS,12bS)-10-((S)-3-(1,3-dithiolan-2-yl)butyl)-6a,8a,9-trimethyl-1,2,2a,3,4,5,6,6a,8a,8b,9,10,11a,12,12a,12b-hexadecahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-8,2'-[1,3]dithiolan]-4-yl acetate
• CAS: 1252023-65-6
• 化学式: C₃₃H₅₀O₃S₄
• 分子量: 623.022
• InChiKey: JCBZSSUEGJMTHQ-WVFUPJMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.52
• 重原子数：
  40.0
• 可旋转键数：
  5.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2aS,4S,6aS,8aS,8bR,9S,10R,11aS,12aS,12bS)-10-((S)-3-(1,3-dithiolan-2-yl)butyl)-6a,8a,9-trimethyl-1,2,2a,3,4,5,6,6a,8a,8b,9,10,11a,12,12a,12b-hexadecahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-8,2'-[1,3]dithiolan]-4-yl acetate 在 乙醇 作用下， 以 乙醚 为溶剂， 反应 19.0h， 以61%的产率得到5α-furost-9(11)-en-3β-ol 3-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
• 作为产物：
  描述：

  1,2-乙二硫醇 、 Δ⁹⁽¹¹⁾22-isoallospirosten-3β-ol-12-one-3-acetate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以87%的产率得到(2aS,4S,6aS,8aS,8bR,9S,10R,11aS,12aS,12bS)-10-((S)-3-(1,3-dithiolan-2-yl)butyl)-6a,8a,9-trimethyl-1,2,2a,3,4,5,6,6a,8a,8b,9,10,11a,12,12a,12b-hexadecahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-8,2'-[1,3]dithiolan]-4-yl 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