3β-acetoxy-5β,17α-pregn-14-ene | 203727-83-7

• 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: 3β-acetoxy-5β,17α-pregn-14-ene
• 英文别名: [(3S,5R,8R,9S,10S,13R,17R)-17-ethyl-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 203727-83-7
• 化学式: C₂₃H₃₆O₂
• 分子量: 344.538
• InChiKey: GQWLWLIRAYCLFU-GJTHSAOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-5β,17α-pregn-14-ene 在 臭氧 、 溶剂黄146 、 锌 作用下， 生成 3β-acetoxy-17α-ethyl-14,15-seco-5β-androstane-14,15-dione
  参考文献：
  名称：

  A New Approach to the Design of Novel Inhibitors of Na⁺,K⁺-ATPase:  17α-Substituted Seco-D 5β-Androstane as Cassaine Analogues

  摘要：

  A new three-dimensional model for the relative binding mode of cassaine 1 and digitoxigenin 2 at the digitalis receptor site is proposed on the basis of the structural and conformational similarities among 1, 2 and its 14,15-seco analogues 3 and 4. Accordingly, the speculation that also 17 alpha-substituted derivatives of the digitalis 5 beta,14 beta-androstane skeleton could efficiently bind to the Na+,K+-ATPase receptor is put forward and verified through the synthesis of some related compounds. The binding affinity shown by 2-(N,N-dimethylamino)ethyl 3 beta,14-dihydroxy-5 beta,14 beta-androstane-17 alpha-acrylate 6 (IC50 = 5.89 mu M) and, much more significantly, by the corresponding 14,15-seco-14-oxo derivative 9 (IC50 = 0.12 mu M) substantiates the new hypothesis and opens new prospects to the design of novel inhibitors of Na+,K+-ATPase as potential positive inotropic compounds.

  DOI：

  10.1021/jm980108d
• 作为产物：
  描述：

  3β-acetoxy-14-hydroxy-5β,14β,17α-pregnane 在 吡啶 、 氯化亚砜 作用下， 反应 1.0h， 以82.2%的产率得到3β-acetoxy-5β,17α-pregn-14-ene
  参考文献：
  名称：

  A New Approach to the Design of Novel Inhibitors of Na⁺,K⁺-ATPase:  17α-Substituted Seco-D 5β-Androstane as Cassaine Analogues

  摘要：

  A new three-dimensional model for the relative binding mode of cassaine 1 and digitoxigenin 2 at the digitalis receptor site is proposed on the basis of the structural and conformational similarities among 1, 2 and its 14,15-seco analogues 3 and 4. Accordingly, the speculation that also 17 alpha-substituted derivatives of the digitalis 5 beta,14 beta-androstane skeleton could efficiently bind to the Na+,K+-ATPase receptor is put forward and verified through the synthesis of some related compounds. The binding affinity shown by 2-(N,N-dimethylamino)ethyl 3 beta,14-dihydroxy-5 beta,14 beta-androstane-17 alpha-acrylate 6 (IC50 = 5.89 mu M) and, much more significantly, by the corresponding 14,15-seco-14-oxo derivative 9 (IC50 = 0.12 mu M) substantiates the new hypothesis and opens new prospects to the design of novel inhibitors of Na+,K+-ATPase as potential positive inotropic compounds.

  DOI：

  10.1021/jm980108d

文献信息

• Seco-d steroids active on the cardiovascular system, processes for their
  申请人：Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.

  公开号：US05955632A1

  公开（公告）日：1999-09-21

  New seco-D steroid derivatives, processes for their preparation and pharmaceutical compositions are provided, which are active on the cardiovascular system. The seco-D steroid derivatives have the following general formula (I): ##STR1##

  提供了新的seco-D类类固醇衍生物，其制备过程和药物组成物，对心血管系统具有活性。这些seco-D类类固醇衍生物具有以下一般式(I)：##STR1##
• New seco-D steroids active on the cardiovascular system, processes for their preparation and pharmaceutical compositions containing them
  申请人：SIGMA-TAU Industrie Farmaceutiche Riunite S.p.A.

  公开号：EP0825177B1

  公开（公告）日：2000-04-05
• US5955632A
  申请人：——

  公开号：US5955632A

  公开（公告）日：1999-09-21