(E)-3-(4-fluorophenyl)-1-[(3S,7S,8S,9S,10R,11R,13S,14S,17S)-3,7,11-trihydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]prop-2-en-1-one | 1201659-00-8

• 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: (E)-3-(4-fluorophenyl)-1-[(3S,7S,8S,9S,10R,11R,13S,14S,17S)-3,7,11-trihydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]prop-2-en-1-one
• CAS: 1201659-00-8
• 化学式: C₂₈H₃₅FO₄
• 分子量: 454.582
• InChiKey: CSFGRXZMZASGPR-YKYJTSLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3β,7α,11α-trihydroxypregn-5-en-20-one 、 对氟苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以89%的产率得到(E)-3-(4-fluorophenyl)-1-[(3S,7S,8S,9S,10R,11R,13S,14S,17S)-3,7,11-trihydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]prop-2-en-1-one
  参考文献：
  名称：

  Synthesis of 3β, 7α, 11α-trihydroxy-pregn-21-benzylidene-5-en-20-one derivatives and their cytotoxic activities

  摘要：

  A series of novel 3 beta, 7 alpha, 11 alpha-trihydroxy-pregn-21-benzylidene-5-en-20-one derivatives were synthesized and characterized by NMR, HRMS. The pregnenolone (1) was first biotransformed by Mucor circinelloides var lusitanicus to 3 beta, 7 alpha, 11 alpha-trihydroxy-pregn-5-en-20-one (3), then 3 was treated with various benzaldehydes to produce 3 beta, 7 alpha, 11 alpha-trihydroxy-pregn-21-benzylidene-5-en-20-one derivatives. These derivatives showed remarkable activity against EC109 cells. The absolute configuration of 3 was also confirmed by signal-crystal X-ray analysis. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.019