(2S,4aS,6S,8aS)-6-((1S,2S,3S)-3-acetyl-2-methyl-2-(2-oxoethyl)cyclopentyl)-4a-methyl-5-oxodecahydronaphthalen-2-yl acetate | 1252023-55-4

• 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: (2S,4aS,6S,8aS)-6-((1S,2S,3S)-3-acetyl-2-methyl-2-(2-oxoethyl)cyclopentyl)-4a-methyl-5-oxodecahydronaphthalen-2-yl acetate
• CAS: 1252023-55-4
• 化学式: C₂₃H₃₄O₅
• 分子量: 390.52
• InChiKey: LXJRVMFKVRAEOD-SZKCUPFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.91
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  77.51
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,4aS,6S,8aS)-6-((1S,2S,3S)-3-acetyl-2-methyl-2-(2-oxoethyl)cyclopentyl)-4a-methyl-5-oxodecahydronaphthalen-2-yl acetate 在 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 0.5h， 以42%的产率得到[(2S,4aS,6S,8aS)-6-[(4aS,5S)-1,4a-dimethyl-4,5,6,7-tetrahydro-3H-cyclopenta[c]pyran-5-yl]-4a-methyl-5-oxo-1,2,3,4,6,7,8,8a-octahydronaphthalen-2-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
• 作为产物：
  描述：

  3β-hydroxy-allopregn-9(11)-en-20-one 3-acetate 在 臭氧 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以73%的产率得到(2S,4aS,6S,8aS)-6-((1S,2S,3S)-3-acetyl-2-methyl-2-(2-oxoethyl)cyclopentyl)-4a-methyl-5-oxodecahydronaphthalen-2-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