3-oxo-5β-estrane-17-ethylene ketal | 876017-48-0

• 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: 3-oxo-5β-estrane-17-ethylene ketal
• 英文别名: (5R,8R,9R,10S,13S,14S)-13-methylspiro[1,2,4,5,6,7,8,9,10,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthrene-17,2'-1,3-dioxolane]-3-one
• CAS: 876017-48-0
• 化学式: C₂₀H₃₀O₃
• 分子量: 318.456
• InChiKey: CLASKVSPOINXBH-FKQYBKHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-oxo-5β-estrane-17-ethylene ketal 在 Lindlar's catalyst 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 正丁基锂 、 potassium tert-butylate 、 水 、 氢气 、 sodium acetate 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 pyridinium hydrobromide perbromide 、 calcium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 、 丙酮 、 甲苯 、 苯 为溶剂， -70.0~60.0 ℃ 、344.74 kPa 条件下， 反应 125.5h， 生成 4-(3'α-benzyloxy-15'β-hydroxy-5'β-estran-17'β-yl)furan-2-carboxyaldehyde ethylene acetal
  参考文献：
  名称：

  4-(3‘α15‘β-Dihydroxy-5‘β-estran-17‘β-yl)furan-2-methyl Alcohol:  An Anti-Digoxin Agent with a Novel Mechanism of Action

  摘要：

  The synthesis and some pharmacological properties of 4-(3'alpha-15'beta-dihydroxy-5 beta-estran-17'beta-yl)furan-2-methyl alcohol (16) have been described. The compound was synthesized by reacting a synthetic 3 alpha-benzyloxy-5 beta-estr-15-en-17-one with the ethylene acetal of 4-bromo-2-furancarboxyaldehyde, followed by hydrolysis of the ethylene acetal and reduction of the aldehyde. Despite its resemblance to the structure of cardiac steroids (CS), 16 does not bind to the CS receptor on Na+,K+-ATPase and does not increase the force of contraction of heart muscle. However, 16 inhibited the digoxin-induced increase in the force of contraction and arrhythmias in guinea pig papillary muscle and human atrial appendages. The steroid also inhibited digoxin-induced alteration in endocytosed membrane traffic, indicating a novel mechanism of action.

  DOI：

  10.1021/jm0505819
• 作为产物：
  描述：

  19-去甲-4-雄烯二酮 在 rhodium(III) chloride 、 氢气 、 碘 、 4-甲基苯磺酸吡啶 、 甲基三辛基氯化铵 作用下， 以 二氯甲烷 、 丙酮 、 苯 为溶剂， 10.0 ℃ 、344.74 kPa 条件下， 反应 0.33h， 生成 3-oxo-5β-estrane-17-ethylene ketal
  参考文献：
  名称：

  4-(3‘α15‘β-Dihydroxy-5‘β-estran-17‘β-yl)furan-2-methyl Alcohol:  An Anti-Digoxin Agent with a Novel Mechanism of Action

  摘要：

  The synthesis and some pharmacological properties of 4-(3'alpha-15'beta-dihydroxy-5 beta-estran-17'beta-yl)furan-2-methyl alcohol (16) have been described. The compound was synthesized by reacting a synthetic 3 alpha-benzyloxy-5 beta-estr-15-en-17-one with the ethylene acetal of 4-bromo-2-furancarboxyaldehyde, followed by hydrolysis of the ethylene acetal and reduction of the aldehyde. Despite its resemblance to the structure of cardiac steroids (CS), 16 does not bind to the CS receptor on Na+,K+-ATPase and does not increase the force of contraction of heart muscle. However, 16 inhibited the digoxin-induced increase in the force of contraction and arrhythmias in guinea pig papillary muscle and human atrial appendages. The steroid also inhibited digoxin-induced alteration in endocytosed membrane traffic, indicating a novel mechanism of action.

  DOI：

  10.1021/jm0505819

文献信息

• 4-(3‘α15‘β-Dihydroxy-5‘β-estran-17‘β-yl)furan-2-methyl Alcohol:  An Anti-Digoxin Agent with a Novel Mechanism of Action
  作者：Joseph Deutsch、Huang G. Jang、Nura Mansur、Ohad Ilovich、Uri Shpolansky、Dana Galili、Tomer Feldman、Haim Rosen、David Lichtstein

  DOI：10.1021/jm0505819

  日期：2006.1.1

  The synthesis and some pharmacological properties of 4-(3'alpha-15'beta-dihydroxy-5 beta-estran-17'beta-yl)furan-2-methyl alcohol (16) have been described. The compound was synthesized by reacting a synthetic 3 alpha-benzyloxy-5 beta-estr-15-en-17-one with the ethylene acetal of 4-bromo-2-furancarboxyaldehyde, followed by hydrolysis of the ethylene acetal and reduction of the aldehyde. Despite its resemblance to the structure of cardiac steroids (CS), 16 does not bind to the CS receptor on Na+,K+-ATPase and does not increase the force of contraction of heart muscle. However, 16 inhibited the digoxin-induced increase in the force of contraction and arrhythmias in guinea pig papillary muscle and human atrial appendages. The steroid also inhibited digoxin-induced alteration in endocytosed membrane traffic, indicating a novel mechanism of action.