3β,14β-dihydroxy-5β-androstane-17α-carbaldehyde | 42548-30-1

• 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: 3β,14β-dihydroxy-5β-androstane-17α-carbaldehyde
• 英文别名: (3S,5R,8R,9S,10S,13R,14S,17R)-3,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-17-carbaldehyde
• CAS: 42548-30-1
• 化学式: C₂₀H₃₂O₃
• 分子量: 320.472
• InChiKey: LYTKTHXGDZMUAY-UVFUQYPRSA-N

物化性质

• 沸点：
  451.3±45.0 °C(Predicted)
• 密度：
  1.189±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Diethyl-2-(dimethylamino)-ethoxycarbonylmethylphosponat 、 3β,14β-dihydroxy-5β-androstane-17α-carbaldehyde 在 sodium hydride 作用下， 生成 2-(dimethylamino)ethyl (E)-3-[(3S,5R,8R,9S,10S,13R,14S,17S)-3,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]prop-2-enoate
  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,14β-dihydroxy-5β-androstane-17β-carboxaldehyde 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以85%的产率得到3β,14β-dihydroxy-5β-androstane-17α-carbaldehyde
  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

• 17α-<i>O</i>-(Aminoalkyl)oxime Derivatives of 3β,14β-Dihydroxy-5β-androstane and 3β-Hydroxy-14-oxoseco-D-5β-androstane as Inhibitors of Na⁺,K⁺-ATPase at the Digitalis Receptor
  作者：Mauro Gobbini、Paolo Barassi、Alberto Cerri、Sergio De Munari、Giorgio Fedrizzi、Marco Santagostino、Antonio Schiavone、Marco Torri、Piero Melloni

  DOI：10.1021/jm0109208

  日期：2001.11.1

  receptor was used to design these compounds. On that basis, the possibility to design novel potent inhibitors of Na(+),K(+)-ATPase without being constrained by the stereochemistry of the classical digitalis skeleton in the D-ring region was predicted. The binding affinities of the most potent compounds in the two series, (EZ)-17 alpha-[2-[(2-aminoethoxy)imino]ethyl]-5 beta-androstane-3 beta,14 beta-diol

  一系列的3 beta，14 beta-dihydroxy-5 beta-雄甾烷和3 beta-hydroxy-14-oxoseco-D-5 beta的洋地黄Na（+），K（+）-ATPase受体的合成和结合亲和力报道了带有17个α-（氨基烷氧基）亚氨基链的-雄甾烷衍生物。还研究了一些衍生物的正性肌力。我们最近提出的分子与洋地黄受体相互作用的模型被用来设计这些化合物。在此基础上，预测了设计新型Na（+），K（+）-ATPase抑制剂的可能性，而不受D环区域经典洋地黄骨架的立体化学的约束。这两个系列中最有效的化合物（EZ）-17 alpha- [2-[（2-氨基乙氧基）亚氨基]乙基] -5β-雄甾烷3β的结合亲和力，14β-二醇（6f）和（EZ）-3β-羟基-17α-[2-[（（2-氨基乙氧基）亚氨基]乙基] -14,15-seco-5β-雄烷-14-一（24c ）比有效的天然化合物洋地黄毒苷