[(3S,8S,9S,10R,13S,14S,17S)-17-[(1E,3E)-5-amino-4-cyano-1-(3,4-difluorophenyl)-5-oxopenta-1,3-dien-3-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate | 1461743-53-2

• 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: [(3S,8S,9S,10R,13S,14S,17S)-17-[(1E,3E)-5-amino-4-cyano-1-(3,4-difluorophenyl)-5-oxopenta-1,3-dien-3-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 1461743-53-2
• 化学式: C₃₃H₃₈F₂N₂O₃
• 分子量: 548.673
• InChiKey: GJTSNTGZBZISFO-GIFOKKCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  40
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  93.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  孕烯醇酮醋酸酯 在 ammonium acetate 、 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 15.0h， 生成 [(3S,8S,9S,10R,13S,14S,17S)-17-[(1E,3E)-5-amino-4-cyano-1-(3,4-difluorophenyl)-5-oxopenta-1,3-dien-3-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
  参考文献：
  名称：

  Stereoselective synthesis of novel antiproliferative steroidal (E, E) dienamides through a cascade aldol/cyclization process

  摘要：

  The stereoselective and metal-free protocol involving a cascade aldol/cyclization process for the synthesis of steroidal (E, E) dienamides from steroidal alpha, alpha-dicyanoalkene was reported. This protocol efficiently achieved the construction of C=C bond and selective conversion of cyano group into carboxamide in one-pot procedure under mild condition. Further biological evaluation showed that some of these compounds had moderate to excellent cytotoxic activities against all the tested cancer cell lines and were more potent than well-known drug 5-fluorouracil. Particularly, compound 3c represented excellent inhibitory effect against MCF-7 (IC50 = 0.76 LM), which was about 10-fold more potent than 5-fluorouracil. (C) 2013 Elsevier Ltd.

  DOI：

  10.1016/j.steroids.2013.08.001