N-(trifluoromethyl)cyclopropyl-3-oxo-4-aza-5α-androst-1-ene-17β-carboxamide | 1431616-39-5

• 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: N-(trifluoromethyl)cyclopropyl-3-oxo-4-aza-5α-androst-1-ene-17β-carboxamide
• 英文别名: (1S,3aS,3bS,5aR,9aR,9bS,11aS)-9a,11a-dimethyl-7-oxo-N-[1-(trifluoromethyl)cyclopropyl]-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide
• CAS: 1431616-39-5
• 化学式: C₂₃H₃₁F₃N₂O₂
• 分子量: 424.507
• InChiKey: XZMDWZUYDFLMRU-ICVGDBTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-三氟甲基环丙胺 、 非那雄胺 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以31%的产率得到N-(trifluoromethyl)cyclopropyl-3-oxo-4-aza-5α-androst-1-ene-17β-carboxamide
  参考文献：
  名称：

  Metabolically Stable tert-Butyl Replacement

  摘要：

  Susceptibility to metabolism is a common issue with the tert-butyl group on compounds of medicinal interest. We demonstrate an approach of removing all the fully sp(3) C-Hs from a tert-butyl group: replacing some C-Hs with C-Fs and increasing the s-character of the remaining C-Hs. This approach gave a trifluoromethylcyclopropyl group, which increased metabolic stability. Trifluoromethylcyclopropyl-containing analogues had consistently higher metabolic stability in vitro and in vivo compared to their tert-butyl-containing counterparts.

  DOI：

  10.1021/ml400045j

文献信息

• Metabolically Stable <i>tert</i>-Butyl Replacement
  作者：David Barnes-Seeman、Monish Jain、Leslie Bell、Suzie Ferreira、Scott Cohen、Xiao-Hui Chen、Jakal Amin、Brad Snodgrass、Panos Hatsis

  DOI：10.1021/ml400045j

  日期：2013.6.13

  Susceptibility to metabolism is a common issue with the tert-butyl group on compounds of medicinal interest. We demonstrate an approach of removing all the fully sp(3) C-Hs from a tert-butyl group: replacing some C-Hs with C-Fs and increasing the s-character of the remaining C-Hs. This approach gave a trifluoromethylcyclopropyl group, which increased metabolic stability. Trifluoromethylcyclopropyl-containing analogues had consistently higher metabolic stability in vitro and in vivo compared to their tert-butyl-containing counterparts.