5-[(3S,5R,8R,9S,10S,13S,14R,17S)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pyran-2-one | 914645-03-7

• 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: 5-[(3S,5R,8R,9S,10S,13S,14R,17S)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pyran-2-one
• CAS: 914645-03-7
• 化学式: C₃₀H₄₈O₃Si
• 分子量: 484.795
• InChiKey: PDYCXDZJJWTPCY-UGYGQXSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.16
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-((3S,5R,8R,9S,10S,13S,14R)-3-((tert-butyldimethylsilyl)oxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2H-pyran-2-one 在 Wilkinson's catalyst 、 氢气 作用下， 以 苯 为溶剂， 生成 5-[(3S,5R,8R,9S,10S,13S,14R,17S)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pyran-2-one
  参考文献：
  名称：

  Selective inhibition of the cellular sodium pump by emicymarin and 14ß anhydroxy bufadienolides

  摘要：

  Partial inhibition of the sodium pump (Na/K-ATP-ase) by a circulating inhibitor is known to occur in humans. The objectives of this study were to determine the effects of novel bufadienolides lacking an oxygen at C14 on sodium pumps in human erythrocytes and leucocytes, dog kidney and pig brain and to document the importance of the stereochemistry at C17 on the ability to inhibit these sodium pumps. 14 alpha bufadienolides were weak inhibitors of all preparations studied. 3 beta-OH,5 beta,14 beta bufadienolide produced near-total inhibition of dog kidney and pig brain Na/K-ATP-ase. Over the same concentration range, it maximally inhibited the sodium pump of erythrocytes by 70% and leucocytes by 47%. The inhibition profile induced in the leucocyte sodium pump deviated significantly from the simple sigmoidal relationship present in the other preparations over the 3 x 10(-5) to 1 x 10(-7) mol/1 concentration range. Allo-emicymarin (17 alpha) was confirmed to be a weak inhibitor of the sodium pump/ATP-ase compared with emicymarin (17 beta) but both were weaker inhibitors of the leucocyte sodium pump than that of the other preparations. Molecules with the C14 in the beta configuration are more efficacious than in the a configuration. In the case of emicymarin, the attachment of the furone at C17 in the a configuration results in substantially weaker inhibitory activity than in the beta configuration, seen in most cardenolides and bufadienolides. Unlike ouabain and bufalin that show no specificity of action in these preparations, 3 beta-OH,5 beta,14 beta bufadienolide selectively inhibits the activity of at least one low-prevalence subset of the leucocyte Na/K-ATP-ase. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2010.07.010

文献信息

• Selective inhibition of the cellular sodium pump by emicymarin and 14ß anhydroxy bufadienolides
  作者：Philip J. Hilton、William McKinnon、Edward C. Gravett、Jean-Marie R. Peron、Christopher M. Frampton、M. Gary Nicholls、Gwyn Lord

  DOI：10.1016/j.steroids.2010.07.010

  日期：2010.12

  Partial inhibition of the sodium pump (Na/K-ATP-ase) by a circulating inhibitor is known to occur in humans. The objectives of this study were to determine the effects of novel bufadienolides lacking an oxygen at C14 on sodium pumps in human erythrocytes and leucocytes, dog kidney and pig brain and to document the importance of the stereochemistry at C17 on the ability to inhibit these sodium pumps. 14 alpha bufadienolides were weak inhibitors of all preparations studied. 3 beta-OH,5 beta,14 beta bufadienolide produced near-total inhibition of dog kidney and pig brain Na/K-ATP-ase. Over the same concentration range, it maximally inhibited the sodium pump of erythrocytes by 70% and leucocytes by 47%. The inhibition profile induced in the leucocyte sodium pump deviated significantly from the simple sigmoidal relationship present in the other preparations over the 3 x 10(-5) to 1 x 10(-7) mol/1 concentration range. Allo-emicymarin (17 alpha) was confirmed to be a weak inhibitor of the sodium pump/ATP-ase compared with emicymarin (17 beta) but both were weaker inhibitors of the leucocyte sodium pump than that of the other preparations. Molecules with the C14 in the beta configuration are more efficacious than in the a configuration. In the case of emicymarin, the attachment of the furone at C17 in the a configuration results in substantially weaker inhibitory activity than in the beta configuration, seen in most cardenolides and bufadienolides. Unlike ouabain and bufalin that show no specificity of action in these preparations, 3 beta-OH,5 beta,14 beta bufadienolide selectively inhibits the activity of at least one low-prevalence subset of the leucocyte Na/K-ATP-ase. (C) 2010 Elsevier Inc. All rights reserved.