18,20-epoxy-20-hydroxy-5α-pregnan-3-one | 14425-53-7

• 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: 18,20-epoxy-20-hydroxy-5α-pregnan-3-one
• 英文别名: (1R,2S,5S,9R,12S,13S,18S)-6-hydroxy-6,13-dimethyl-7-oxapentacyclo[10.8.0.02,9.05,9.013,18]icosan-16-one
• CAS: 14425-53-7
• 化学式: C₂₁H₃₂O₃
• 分子量: 332.483
• InChiKey: GQKUJAPLKAESKA-JFMMBHASSA-N

物化性质

• 熔点：
  159-160 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  473.9±40.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  18,20-epoxy-20-hydroxy-5α-pregnan-3-one 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 18,21-dihydroxy-5α-pregnane-3,20-dione 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：

  别孕烯醇酮醋酸酯 在 吡啶 、 chromium(VI) oxide 、 甲醇 、 氢氧化钾 、 lithium tri-t-butoxyaluminum hydride 作用下， 生成 18,20-epoxy-20-hydroxy-5α-pregnan-3-one
  参考文献：
  名称：

  Takegoshi,T., Chemical and pharmaceutical bulletin, 1972, vol. 20, # 6, p. 1260 - 1271

  摘要：

  DOI：

文献信息

• Takegoshi,T., Chemical and pharmaceutical bulletin, 1972, vol. 20, # 6, p. 1260 - 1271
  作者：Takegoshi,T.

  DOI：——

  日期：——
• Mineralocorticoid properties of potential metabolites of 18-hydroxydeoxycorticosterone and 18-hydroxyprogesterone
  作者：John F. Weet、George R. Lenz

  DOI：10.1021/jm00380a014

  日期：1985.2

  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.