(3β,5β,8α,10α,13α,14β)-3-hydroxyandrost-9(11)-en-17-one, cyclic 17-(1,2-ethanediyl acetal) | 1355032-19-7

• 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: (3β,5β,8α,10α,13α,14β)-3-hydroxyandrost-9(11)-en-17-one, cyclic 17-(1,2-ethanediyl acetal)
• 英文别名: (3S,5R,8R,10R,13R,14R)-10,13-dimethylspiro[1,2,3,4,5,6,7,8,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-17,2'-1,3-dioxolane]-3-ol
• CAS: 1355032-19-7
• 化学式: C₂₁H₃₂O₃
• 分子量: 332.483
• InChiKey: TVKKFJYLCTVMTE-OTCXFQBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3β,5β,8α,10α,13α,14β)-3-hydroxyandrost-9(11)-en-17-one, cyclic 17-(1,2-ethanediyl acetal) 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 硼烷四氢呋喃络合物 、 sodium acetate 、 potassium hydride 、 N,N-二异丙基乙胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 mineral oil 为溶剂， 反应 47.0h， 生成 (3β,5β,8α,9β,10α,11α,13α,14β)-11-(benzyloxy)-3-[[(methyloxy)methyl]oxy]androstan-17-one, cyclo 17-(1,2-ethanediyl acetal)
  参考文献：
  名称：

  Neurosteroid Analogues. 17. Inverted Binding Orientations of Androsterone Enantiomers at the Steroid Potentiation Site on γ-Aminobutyric Acid Type A Receptors

  摘要：

  The enantiomer pair androsterone and ent-androsterone are positive allosteric modulators of gamma-aminobutyric acid (GABA) type A receptors. Each enantiomer was shown to bind at the same receptor site. Binding orientations of the enantiomers at this site were deduced using enantiomer pairs containing OBn substituents at either C-7 or C-11. 11 beta-OBn-substituted steroids and 7 alpha-OBn-substituted ent-steroids potently displace [S-35]-tert-butylbicyclophosphorothionate, augment GABA currents, and anesthetize tadpoles. In contrast, 7 beta-OBn-substituted steroids and 11 alpha-OBn-substituted ent-steroids have diminished actions. The results suggest that the binding orientations of the active analogues are inverted relative to each other with the 7 alpha- and 11 beta-substituents similarly located on the edges of the molecules not in contact with the receptor surface. Analogue potentiation of the GABA current was abrogated by an alpha(1) subunit Q241L mutation, indicating that the active analogues act at the same sites in alpha(1)beta(2)gamma(2L) receptors previously associated with positive neurosteroid modulation.

  DOI：

  10.1021/jm2014925
• 作为产物：
  描述：

  (5β,8α,10α,13α,14β)-androst-9(11)-ene-3,17-dione 在 4-甲基苯磺酸吡啶 、 potassium tri-sec-butyl-borohydride 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 17.5h， 生成 (3β,5β,8α,10α,13α,14β)-3-hydroxyandrost-9(11)-en-17-one, cyclic 17-(1,2-ethanediyl acetal)
  参考文献：
  名称：

  Neurosteroid Analogues. 17. Inverted Binding Orientations of Androsterone Enantiomers at the Steroid Potentiation Site on γ-Aminobutyric Acid Type A Receptors

  摘要：

  The enantiomer pair androsterone and ent-androsterone are positive allosteric modulators of gamma-aminobutyric acid (GABA) type A receptors. Each enantiomer was shown to bind at the same receptor site. Binding orientations of the enantiomers at this site were deduced using enantiomer pairs containing OBn substituents at either C-7 or C-11. 11 beta-OBn-substituted steroids and 7 alpha-OBn-substituted ent-steroids potently displace [S-35]-tert-butylbicyclophosphorothionate, augment GABA currents, and anesthetize tadpoles. In contrast, 7 beta-OBn-substituted steroids and 11 alpha-OBn-substituted ent-steroids have diminished actions. The results suggest that the binding orientations of the active analogues are inverted relative to each other with the 7 alpha- and 11 beta-substituents similarly located on the edges of the molecules not in contact with the receptor surface. Analogue potentiation of the GABA current was abrogated by an alpha(1) subunit Q241L mutation, indicating that the active analogues act at the same sites in alpha(1)beta(2)gamma(2L) receptors previously associated with positive neurosteroid modulation.

  DOI：

  10.1021/jm2014925