(5R,8S,10S,13S,14S,16R,17R)-17-Hydroxy-10,13,16-trimethyl-17-[2-(4-pyridin-2-yl-piperazin-1-yl)-acetyl]-1,2,4,5,6,7,8,10,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one | 125276-13-3

• 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: (5R,8S,10S,13S,14S,16R,17R)-17-Hydroxy-10,13,16-trimethyl-17-[2-(4-pyridin-2-yl-piperazin-1-yl)-acetyl]-1,2,4,5,6,7,8,10,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one
• CAS: 125276-13-3
• 化学式: C₃₁H₄₃N₃O₃
• 分子量: 505.701
• InChiKey: VIYHEKHUQRMKKC-QUPUOXPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.28
• 重原子数：
  37.0
• 可旋转键数：
  4.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  73.74
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  1-(2-吡啶基)哌嗪 、 (5R,8S,10S,13S,14S,16R,17R)-17-(2-Bromo-acetyl)-17-hydroxy-10,13,16-trimethyl-1,2,4,5,6,7,8,10,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以88%的产率得到(5R,8S,10S,13S,14S,16R,17R)-17-Hydroxy-10,13,16-trimethyl-17-[2-(4-pyridin-2-yl-piperazin-1-yl)-acetyl]-1,2,4,5,6,7,8,10,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one
  参考文献：
  名称：

  Novel 21-aminosteroids that inhibit iron-dependent lipid peroxidation and protect against central nervous system trauma

  摘要：

  A novel class of 21-aminosteroids has been developed. Compounds within this series are potent inhibitors of iron-dependent lipid peroxidation in rat brain homogenates with IC50's as low as 3 microM. Furthermore, selected members enhance early neurological recovery and survival in a mouse head injury model. Significant improvement in the 1 h post-head-injury neurological status (grip test score) by as much as 168.6% of the control has been observed. The most efficacious compound in this assay (30) showed an increase in the 1-week survival of 78.6% as compared to 27.3% for the vehicle-treated mice in the head-injury model. Based on its biological profile, 21-[4-(2,6-di-1-pyrrolidinyl-4-pyrimidinyl)-1-piperazinyl]-16 alpha- methylpregna-1,4,9(11)-triene-3,20-dione monomethanesulfonate (30) was selected for further evaluation and is currently entering phase I clinical trials for the treatment of head and spinal trauma.

  DOI：

  10.1021/jm00166a010