(8S,10S,13S,14S,16R,17S)-10,13,16-Trimethyl-17-[2-(4-pyridin-2-yl-piperazin-1-yl)-acetyl]-6,7,8,10,12,13,14,15,16,17-decahydro-cyclopenta[a]phenanthren-3-one | 111667-71-1

• 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,10S,13S,14S,16R,17S)-10,13,16-Trimethyl-17-[2-(4-pyridin-2-yl-piperazin-1-yl)-acetyl]-6,7,8,10,12,13,14,15,16,17-decahydro-cyclopenta[a]phenanthren-3-one
• 英文别名: (8S,10S,13S,14S,16R,17S)-10,13,16-trimethyl-17-[2-(4-pyridin-2-ylpiperazin-1-yl)acetyl]-6,7,8,12,14,15,16,17-octahydrocyclopenta[a]phenanthren-3-one
• CAS: 111667-71-1
• 化学式: C₃₁H₃₉N₃O₂
• 分子量: 485.67
• InChiKey: WPIUGWPHZRJCKU-CHQCSSIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  53.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  16α-methyl-21-hydroxypregna-1,4,9(11)-triene-3,20-dione 在 potassium carbonate 、 三乙胺 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 44.0h， 生成 (8S,10S,13S,14S,16R,17S)-10,13,16-Trimethyl-17-[2-(4-pyridin-2-yl-piperazin-1-yl)-acetyl]-6,7,8,10,12,13,14,15,16,17-decahydro-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

文献信息

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

  公开号：WO1987001706A2

  公开（公告）日：1987-03-26

  (EN) Disclosed are $g(D)9(11)-steroids (VI) and amino substituted steroids of formula (XI), which contain an amino group attached to the terminal carbon atom of the C17-side chain, more particularly amino steroids (Ia and Ib), aromatic steroids (II), $g(D)16-steroids (IIIa and IIIb), reduced A-ring steroids (IV), $g(D)17(20)-steroids (Va and Vb) and $g(D)9(11)-steroids (VI) which are useful as pharmaceutical agents for treating a number of conditions.(FR) Stéroïdes $g(D)9(11) (VI) et stéroïdes à substitution amino de formule (XI), contenant un groupe amino fixé à la terminaison d'atome de carbone de la chaîne côté C17, plus particulièrement amino-stéroïdes (Ia et Ib), stéroïdes aromatiques (II), stéroïdes $g(D)16 IIIa et IIIb), stéroïdes à composés cycliques A réduits (IV), stéroïdes $g(D)17(20) (Va et Vb) et stéroïdes $g(D)9(11) (VI) utiles en tant qu'agents pharmaceutiques pour traiter un certain nombre d'états.

  揭示了$g(D)9(11)-类固醇(VI)和式子(XI)的氨基取代类固醇，其中包含连接到C17侧链末端碳原子的氨基基团，更具体地包括氨基类固醇(Ia和Ib)，芳香族类固醇(II)，$g(D)16-类固醇(IIIa和IIIb)，还原A环类固醇(IV)，$g(D)17(20)-类固醇(Va和Vb)和$g(D)9(11)-类固醇(VI)，这些类固醇可用作治疗多种疾病的药物。
• C20 Through C26 amino steroids
  申请人：THE UPJOHN COMPANY

  公开号：EP0263213B1

  公开（公告）日：1995-09-06
• C20 THROUGH C26 AMINO STEROIDS
  申请人：THE UPJOHN COMPANY

  公开号：EP0238545B1

  公开（公告）日：1995-11-15
• C 20? THROUGH C 26? AMINO STEROIDS
  申请人：THE UPJOHN COMPANY

  公开号：EP0238545A1

  公开（公告）日：1987-09-30
• US5380841A
  申请人：——

  公开号：US5380841A

  公开（公告）日：1995-01-10