3α-hydroxy-16α-(2,3-dihydroxypropoxy)-5α-pregnan-20-one | 1140441-28-6

• 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: 3α-hydroxy-16α-(2,3-dihydroxypropoxy)-5α-pregnan-20-one
• 英文别名: 1-[(3R,5S,8R,9S,10S,13S,14S,16R,17R)-16-(2,3-dihydroxypropoxy)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
• CAS: 1140441-28-6
• 化学式: C₂₄H₄₀O₅
• 分子量: 408.579
• InChiKey: OJRBOIBGIOSXAN-XLMUXUMYSA-N

物化性质

• 熔点：
  174-175 °C(Solvent: Acetone; Heptane)
• 沸点：
  577.5±40.0 °C(predicted)
• 密度：
  1.17±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  、 甘油 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 48.0h， 以90%的产率得到3α-Hydroxy-5α-pregn-16-en-20-one
  参考文献：
  名称：

  Allopregnanolone (3α-Hydroxy-5α-pregnan-20-one) Derivatives with a Polar Chain in Position 16α: Synthesis and Activity

  摘要：

  The lipophilic nature of allopregnanolone prevents its user-friendly application in human medicine. On inspiration by previously prepared allopregnanolone with a 16 alpha-bound tetraethylammonium salt, an attempt was made to produce allopregnanolone analogues with polar groups introduced into position 16 alpha with the goal of increasing water solubility, brain accessibility, and potency of neuroactive steroids. The Michael addition to derivatives of pregn-16-en-20-one was the key reaction step. The link between the steroid skeleton and the new side chain was either a methylene group (when diethyl malonate was added) or an oxygen atom (when a hydroxy derivative was added). [S-35]TBPS displacement was used to evaluate the products. Several carbamates (but not their parent alcohols) displaced TBPS from the picrotoxin binding site on GABA(A) receptors. Although none of them was more potent than the above ammonium salt, which stimulated this study, their nonionic nature should not prevent their passage into the brain.

  DOI：

  10.1021/jm801454a

文献信息

• Allopregnanolone (3α-Hydroxy-5α-pregnan-20-one) Derivatives with a Polar Chain in Position 16α: Synthesis and Activity
  作者：Barbora Slavíková、Zdena Krištofíková、Hana Chodounská、Miloš Buděšínský、Fernando J. Durán、Adriana S. Veleiro、Gerardo Burton、Alexander Kasal

  DOI：10.1021/jm801454a

  日期：2009.4.9

  The lipophilic nature of allopregnanolone prevents its user-friendly application in human medicine. On inspiration by previously prepared allopregnanolone with a 16 alpha-bound tetraethylammonium salt, an attempt was made to produce allopregnanolone analogues with polar groups introduced into position 16 alpha with the goal of increasing water solubility, brain accessibility, and potency of neuroactive steroids. The Michael addition to derivatives of pregn-16-en-20-one was the key reaction step. The link between the steroid skeleton and the new side chain was either a methylene group (when diethyl malonate was added) or an oxygen atom (when a hydroxy derivative was added). [S-35]TBPS displacement was used to evaluate the products. Several carbamates (but not their parent alcohols) displaced TBPS from the picrotoxin binding site on GABA(A) receptors. Although none of them was more potent than the above ammonium salt, which stimulated this study, their nonionic nature should not prevent their passage into the brain.