(8S,9S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-17-[2-(4-pyridin-2-ylpiperazin-1-yl)acetyl]-1,2,6,7,8,9,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,11-dione | 111640-53-0

• 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: (8S,9S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-17-[2-(4-pyridin-2-ylpiperazin-1-yl)acetyl]-1,2,6,7,8,9,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,11-dione
• CAS: 111640-53-0
• 化学式: C₃₀H₃₉N₃O₄
• 分子量: 505.657
• InChiKey: ZBMADTDCHDLKOH-DXQCBORDSA-N

物化性质

• 熔点：
  154-157 °C
• 沸点：
  698.0±55.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  37
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  90.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-(2-吡啶基)哌嗪 、 21-bromo-17α-hydroxy-4-pregnene-3,11,20-trione 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以54%的产率得到(8S,9S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-17-[2-(4-pyridin-2-ylpiperazin-1-yl)acetyl]-1,2,6,7,8,9,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,11-dione
  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

文献信息

• C20 THROUGH C26 AMINO STEROIDS
  申请人：THE UPJOHN COMPANY

  公开号：EP0238545B1

  公开（公告）日：1995-11-15