3β,20(R)-dihydroxy-5α-pregnan-18-oic acid γ-lactone | 1238-51-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 3β,20(R)-dihydroxy-5α-pregnan-18-oic acid γ-lactone
• CAS: 1238-51-3
• 化学式: C₂₁H₃₂O₃
• 分子量: 332.483
• InChiKey: QOQOHWIHMCTUKL-OAFIPRQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 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：
  0.95
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3β,20(R)-dihydroxy-5α-pregnan-18-oic acid γ-lactone 在 吡啶 、 sodium hydroxide 、 bis(2-methoxyethoxy)aluminum hydride 、 sodium acetate 、 4-甲基苯磺酸吡啶 、 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 26.25h， 生成 Pregnane-3,20-diol, 18,20-epoxy-, (3b,5a)-
  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：

  3β-hydroxy-18:20-epoxy-pregn-5-ene-18-one 在 palladium on activated charcoal 吡啶 、 sodium hydroxide 、 氢气 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 25.0~60.0 ℃ 、413.69 kPa 条件下， 反应 6.0h， 生成 3β,20(R)-dihydroxy-5α-pregnan-18-oic acid γ-lactone
  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

文献信息

• Intramolecular hydride shift in Oppenauer oxidation of some dihydroxy steroids
  作者：L. Eignerová、A. Kasal

  DOI：10.1135/cccc19761056

  日期：——