3β,20β-dihydroxypregn-5-en-18-oic acid 18,20-lactone 3-acetate | 3020-10-8

• 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: 3β,20β-dihydroxypregn-5-en-18-oic acid 18,20-lactone 3-acetate
• 英文别名: (20R)-3β-acetoxypregn-5-eno-20,18-lactone；[(1R,2S,5S,6R,9R,12S,13R,16S)-6,13-dimethyl-8-oxo-7-oxapentacyclo[10.8.0.02,9.05,9.013,18]icos-18-en-16-yl] acetate
• CAS: 3020-10-8
• 化学式: C₂₃H₃₂O₄
• 分子量: 372.505
• InChiKey: BZNVCRMVTJWPOI-GFUYTTEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  27.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3β,20β-dihydroxypregn-5-en-18-oic acid 18,20-lactone 3-acetate 在 palladium on activated charcoal 吡啶 、 sodium hydroxide 、 bis(2-methoxyethoxy)aluminum hydride 、 氢气 、 sodium acetate 、 4-甲基苯磺酸吡啶 、 对甲苯磺酸 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 异丙醇 、 甲苯 、 苯 为溶剂， -20.0~60.0 ℃ 、413.69 kPa 条件下， 反应 32.25h， 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：

  乙酸酐 、 3β-hydroxy-18:20-epoxy-pregn-5-ene-18-one 在 吡啶 作用下， 生成 3β,20β-dihydroxypregn-5-en-18-oic acid 18,20-lactone 3-acetate
  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

• Synthesis of [19-2H3]progesterone and [18-2H3]progesterone
  作者：David N. Kirk、Carmen Z. Smith、Michael J. Varley、John W. Honour

  DOI：10.1039/p19900002745

  日期：——

  [19-2H3]Progesterone has been prepared from 3,3 : 20,20-bisethylenedioxy[19-2H3]pregn-5-en-19-ol by reduction of the derived 19-toluene-p-sulphonate with lithium triethylborodeuteride (‘superdeuteride’) followed by hydrolysis of the ethylenedioxy groups. [18-2H3] Progesterone was obtained from (20R)-3β-acetoxy-pregn-5-eno-20,18-lactone via conversion into methyl (20R)-3β-20-dihydroxypregn-5-en-18-oate:

  [19- 2 ħ 3 ]孕酮已经从3,3：20,20- bisethylenedioxy [19- 2 ħ 3〕孕甾-5-烯-19-醇通过还原的衍生19-甲苯p -磺酸盐与三乙基硼氢化氘化锂（“超氘化”），然后乙二氧基水解。[18- 2 ħ 3 ]孕酮从（20获得ř）-3β乙酰氧基孕甾-5- ENO-20,18内酯经由转化为甲基（20 - [R）-3β-20二羟基-5-烯18 -酸酯：两阶段引入氘的三个原子中的C-18通过在甲苯p派生[18-的-磺酸盐2H 2 ] -18-ol需要特殊的实验条件。
• Synthesis of the 13,17 side chain switched isomers of 18-hydroxy- and 18-oxoprogesterone and -deoxycorticosterone
  作者：George R. Lenz、Clifford R. Dorn

  DOI：10.1021/jo00164a013

  日期：1983.8
• KIRK, DAVID N.;SMITH, CARMEN Z.;VARLEY, MICHAEL J.;HONOUR, JOHN W., J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N0, C. 2745-2748
  作者：KIRK, DAVID N.、SMITH, CARMEN Z.、VARLEY, MICHAEL J.、HONOUR, JOHN W.

  DOI：——

  日期：——