3β-Acetoxy-14-hydroxy-5β,14β-pregnan-20-on | 10005-75-1

• 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-Acetoxy-14-hydroxy-5β,14β-pregnan-20-on
• 英文别名: Pregnan-20-one, 3-(acetyloxy)-14-hydroxy-, (3beta,5beta,14beta)-；[(3S,5R,8R,9S,10S,13R,14S,17S)-17-acetyl-14-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl] acetate
• CAS: 10005-75-1
• 化学式: C₂₃H₃₆O₄
• 分子量: 376.536
• InChiKey: XMMWYJKJRBYBKW-UUSJCSPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3β-Acetoxy-14-hydroxy-5β,14β-pregnan-20-on 在 咪唑 、 lithium aluminium tetrahydride 、 lithium tri(t-butoxy)aluminum hydride 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 20β-<(tert-butyldimethylsilyl)oxy>-3β,14-dihydroxy-5β,14β-pregnane
  参考文献：
  名称：

  Cardiac glycoside-like structure and function of 5.beta.,14.beta.-pregnanes

  摘要：

  5 beta-Reduction and 14 beta-substitution convert the planar progesterone molecule to the cardiac glycoside configuration--A and D rings of the steroid moiety are bent toward the alpha-face relative to the B and C rings. Potency of the 5 beta,14 beta-derivative in a [3H]ouabain binding assay or its ability to inhibit the sodium pump in red blood cells is enhanced by 3 beta-hydroxylation, 20 beta-hydroxylation, and 3 beta-glycosidation. Synthesis of 14,20 beta-dihydroxy-3 beta-(beta-D-glucopyranosyloxy)- 5 beta,14 beta-pregnane from digitoxin is described. The glucoside is 1/20 as potent as ouabain and elicits prominent, sustained, positive inotropy in isolated cardiac muscle.

  DOI：

  10.1021/jm00128a047
• 作为产物：
  描述：

  洋地黄毒苷元-3-乙酸酯 在 臭氧 、 溶剂黄146 、 锌 作用下， 生成 3β-Acetoxy-14-hydroxy-5β,14β-pregnan-20-on
  参考文献：
  名称：

  Templeton, John F.; Ling, Yangzhi; Jin, Jichun, Journal of the Chemical Society. Perkin transactions I, 1991, # 4, p. 823 - 829

  摘要：

  DOI：

文献信息

• 13C NMR spectra of 5β,14β-hydroxysteroids
  作者：Gerhard G. Habermehl、Peter E. Hammann、Victor Wray

  DOI：10.1002/mrc.1260231115

  日期：1985.11

  The 13C chemical shifts of 30 substituted 5β,14β-hydroxysteroids are described and discussed. Substituent chemical shifts for 12α- and 12β-hydroxy groups were evaluated, and interesting γ effects were observed. A correlation is shown to exist between the 1H shifts of H-17 and the 13C shifts of C-17 for various C-12 substituents. A relationship for the distance of the substituent at C-12 from H-17 in the 14β,20-lactones was demonstrated, where an increased distance between these atoms is associated with smaller shift differences.

  描述并讨论了 30 种取代的 5β,14β-羟基类固醇的 13C 化学位移。评估了 12α-和 12β-羟基的取代基化学位移，并观察到有趣的 γ 效应。对于各种 C-12 取代基，H-17 的 1H 位移和 C-17 的 13C 位移之间存在相关性。证明了 14β,20-内酯中 C-12 处取代基距 H-17 的距离的关系，其中这些原子之间的距离增加与较小的位移差异相关。
• A pregnane glycoside from Streblus asper
  作者：Kamal Prakash、Desh Deepak、Anakshi Khare、Maheshwari P. Khare

  DOI：10.1016/0031-9422(92)80075-p

  日期：1992.3
• A New Approach to the Design of Novel Inhibitors of Na⁺,K⁺-ATPase:  17α-Substituted Seco-D 5β-Androstane as Cassaine Analogues
  作者：Sergio De Munari、Paolo Barassi、Alberto Cerri、Giorgio Fedrizzi、Mauro Gobbini、Massimo Mabilia、Piero Melloni

  DOI：10.1021/jm980108d

  日期：1998.7.1

  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.
• Theil, Fritz; Lindig, Claus; Repke, Kurt, Zeitschrift fur Chemie, 1980, vol. 20, # 10, p. 372 - 373
  作者：Theil, Fritz、Lindig, Claus、Repke, Kurt

  DOI：——

  日期：——
• <b>The Synthesis of Digitoxigenin</b>
  作者：Naftali. Danieli、Yehuda. Mazur、Franz. Sondheimer

  DOI：10.1021/ja00864a048

  日期：1962.3