Pregnane-3,20-diol, 18,20-epoxy-, (3a,5b)- | 1900-47-6

• 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: Pregnane-3,20-diol, 18,20-epoxy-, (3a,5b)-
• 英文别名: 18,20-epoxy-5β-pregnane-3α,20-diol
• CAS: 1900-47-6
• 化学式: C₂₁H₃₄O₃
• 分子量: 334.499
• InChiKey: OPBWRTJTMOOQDF-ISFCAIHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.73
• 重原子数：
  24.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.69
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  Pregnane-3,20-diol, 18,20-epoxy-, (3a,5b)- 在 氢氧化钾 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 1.25h， 生成 3α,18,21-trihydroxy-5β-pregnane-20-one 18,20-hemiacetal
  参考文献：
  名称：

  Mineralocorticoid properties of potential metabolites of 18-hydroxydeoxycorticosterone and 18-hydroxyprogesterone

  摘要：

  The high secretion rate of 18-hydroxydeoxycorticosterone in hypertensives and the steroids implication as a mineralocorticoid has led to the synthesis of potential di-, tetra-, and hexahydro metabolites of it and 18-hydroxy-progesterone. These potential metabolites have been synthesized by reduction of the double bond and the 3- and 20-ketones, singly or in combination. They have been evaluated for pro- and antimineralocorticoid activity and their affinity for the renal aldosterone receptor. All except one of the potential metabolites either lack or have reduced mineralocorticoid activity and aldosterone receptor binding affinity. The exception is the 3-ketopregn-4-ene-18,20-diol which has high receptor affinity but functions as an aldosterone antagonist.

  DOI：

  10.1021/jm00380a014
• 作为产物：
  描述：

  (3R,3aS,5aS,5bR,7aR,9R,11aS,11bS,13aR)-3,11a-Dimethyl-9-(tetrahydro-pyran-2-yloxy)-hexadecahydro-2-oxa-pentaleno[1,6a-a]phenanthren-1-one 在 吡啶 、 甲醇 、 sodium hydroxide 、 bis(2-methoxyethoxy)aluminum hydride 、 sodium acetate 、 对甲苯磺酸 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 25.0h， 生成 Pregnane-3,20-diol, 18,20-epoxy-, (3a,5b)-
  参考文献：
  名称：

  Mineralocorticoid properties of potential metabolites of 18-hydroxydeoxycorticosterone and 18-hydroxyprogesterone

  摘要：

  The high secretion rate of 18-hydroxydeoxycorticosterone in hypertensives and the steroids implication as a mineralocorticoid has led to the synthesis of potential di-, tetra-, and hexahydro metabolites of it and 18-hydroxy-progesterone. These potential metabolites have been synthesized by reduction of the double bond and the 3- and 20-ketones, singly or in combination. They have been evaluated for pro- and antimineralocorticoid activity and their affinity for the renal aldosterone receptor. All except one of the potential metabolites either lack or have reduced mineralocorticoid activity and aldosterone receptor binding affinity. The exception is the 3-ketopregn-4-ene-18,20-diol which has high receptor affinity but functions as an aldosterone antagonist.

  DOI：

  10.1021/jm00380a014