Acetic acid (3S,5R,8R,9S,10S,13R,14S,16S,17S)-3-acetoxy-17-(2,2-dibromo-5-oxo-2,5-dihydro-furan-3-yl)-14-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-16-yl ester | 96564-22-6

• 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: Acetic acid (3S,5R,8R,9S,10S,13R,14S,16S,17S)-3-acetoxy-17-(2,2-dibromo-5-oxo-2,5-dihydro-furan-3-yl)-14-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-16-yl ester
• 英文别名: [(3S,5R,8R,9S,10S,13R,14S,16S,17S)-16-acetyloxy-17-(2,2-dibromo-5-oxofuran-3-yl)-14-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl] acetate
• CAS: 96564-22-6
• 化学式: C₂₇H₃₆Br₂O₇
• 分子量: 632.387
• InChiKey: FXSOCKCECAKSOA-QWFCBYAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.16
• 重原子数：
  36.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  99.13
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (3S,5R,8R,9S,10S,13R,14S,16S,17S)-3-acetoxy-17-(2,2-dibromo-5-oxo-2,5-dihydro-furan-3-yl)-14-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-16-yl ester 、 甲胺 生成 14-hydroxy-17β-(1,2-N-methylcarbamoylvinyl)-5β,14β-androstane-3β,16β-diyl diacetate
  参考文献：
  名称：

  MEGGES, R.;ROLLKA, W.;WEILAND, J.;FRANKE, P.;HINTSCHE, R.

  摘要：

  DOI：
• 作为产物：
  描述：

  [(3S,5R,8R,9S,10S,13R,14S,16S,17S)-16-acetyloxy-14-hydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl] acetate 、 N-溴代丁二酰亚胺(NBS) 生成 Acetic acid (3S,5R,8R,9S,10S,13R,14S,16S,17S)-3-acetoxy-17-(2,2-dibromo-5-oxo-2,5-dihydro-furan-3-yl)-14-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-16-yl ester
  参考文献：
  名称：

  MEGGES, R.;ROLLKA, W.;WEILAND, J.;FRANKE, P.;HINTSCHE, R.

  摘要：

  DOI：

文献信息

• Cardenamides from Cardenolides: Cardiac and Anticancer Activities
  作者：Rudolf Megges、Jürgen Weiland、Rudolf Schön、Heinrich Repke、Kurt R. H. Repke

  DOI：10.1135/cccc20020336

  日期：——

  Two ways are shown to transform cardioactive cardenolides into cardenamides [17β-(5-oxo-2,5-dihydropyrrol-3-yl)-5β,14β-androstane derivatives], and their derivatives by replacement of their ring oxygen by N-R. Cardioactivity is strongly decreased by this transformation. The comparatively easily accessible 21-oxocardenamides [17β-(2-maleimidyl)steroids] are strongly thiol reactive and show remarkable anticancer activity.

  展示了两种将心脏活性心苷转化为卡德纳胺类化合物[17β-(5-氧代-2,5-二氢吡咯-3-基)-5β,14β-雄甾烷衍生物]及其衍生物的方法，通过用N-R替换其环氧基。这种转化会大大降低心脏活性。相对容易获取的21-氧代卡德纳胺类化合物[17β-(2-马来酰亚胺基)类固醇]具有很强的巯基反应性，并表现出显著的抗癌活性。
• Hintsche; Megges; Pfeiffer, European Journal of Medicinal Chemistry, 1985, vol. 20, # 1, p. 9 - 15
  作者：Hintsche、Megges、Pfeiffer、et al.

  DOI：——

  日期：——