3β-hydroxy-5-methyl-19-nor-5β-pregnan-20-one | 182075-43-0

• 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-hydroxy-5-methyl-19-nor-5β-pregnan-20-one
• 英文别名: 1-[(3S,5R,8R,9S,10R,13S,14S,17S)-3-hydroxy-5,13-dimethyl-2,3,4,6,7,8,9,10,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
• CAS: 182075-43-0
• 化学式: C₂₁H₃₄O₂
• 分子量: 318.5
• InChiKey: RDFMQBKOMXNOIG-LGLBSWAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3β-hydroxy-5-methyl-19-nor-5β-pregnan-20-one 在 jones reagent 作用下， 以 丙酮 为溶剂， 生成 5-methyl-19-nor-5β,9α,10β-pregnane-3,20-dione
  参考文献：
  名称：

  Hydrogenation of a Tetrasubstituted Double Bond: Synthesis of 5-Methyl-19-nor-5β-pregnanes

  摘要：

  5-甲基-19-去氢-5β-孕-9-烯-3,20-二酮（1）中C=C和/或C=O键的还原会产生饱和和不饱和的酮和羟基酮。C=C的还原主要得到9β,10β和9α,10β二氢产物。详细阐述了部分酯化、水解和氧化的反应条件。制备了几种类似物用于测试孕激素和神经类固醇活性。

  DOI：

  10.1135/cccc19981549
• 作为产物：
  描述：

  3β-acetoxy-5-methyl-19-nor-5β-pregn-9-en-20-one 在 platinum(IV) oxide jones reagent 、 水 、 氢气 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 28.0h， 生成 3β-hydroxy-5-methyl-19-nor-5β-pregnan-20-one
  参考文献：
  名称：

  Hydrogenation of a Tetrasubstituted Double Bond: Synthesis of 5-Methyl-19-nor-5β-pregnanes

  摘要：

  5-甲基-19-去氢-5β-孕-9-烯-3,20-二酮（1）中C=C和/或C=O键的还原会产生饱和和不饱和的酮和羟基酮。C=C的还原主要得到9β,10β和9α,10β二氢产物。详细阐述了部分酯化、水解和氧化的反应条件。制备了几种类似物用于测试孕激素和神经类固醇活性。

  DOI：

  10.1135/cccc19981549

文献信息

• Neurosteroid Analogues. 4. The Effect of Methyl Substitution at the C-5 and C-10 Positions of Neurosteroids on Electrophysiological Activity at GABA_A Receptors
  作者：Mingcheng Han、Charles F. Zorumski、Douglas F. Covey

  DOI：10.1021/jm960304p

  日期：1996.1.1

  A series of analogues of the neuroactive steroids 3 alpha-hydroxy-5 alpha-pregnan-20-one and 3 alpha-hydroxy-5 beta-pregnan-20-one were studied to elucidate the mode of binding of 5 alpha- and 5 beta-reduced steroids to steroid binding sites on GABA(A) receptors. Analogues which were either 3 alpha-hydroxy-20-ketosteroids or 3 alpha-hydroxysteroid-17 beta-carbonitriles and which contained various methyl group substitution patterns at C-5 and C-10 were prepared. Evaluations utilized whole-cell patch clamp electrophysiological methods carried out on cultured rat hippocampal neurons, and the results obtained with the rigid 17 beta-carbonitrile analogs were analyzed using molecular modeling methods. The molecular modeling results provide a rationale for the observation that the configuration of the hydroxyl group at C-3 is a greater determinant of anesthetic potency than the configuration of the A,B ring fusion at C-5. The electrophysiological results identify steric restrictions for the space that can be occupied in 5 alpha- and 5 beta-reduced steriod modulators of GABA(A) receptors in the regions of space proximate to the steroid C-5, C-10, and possibly C-4 positions. This information is useful for the development of nonsteroidal analogues that can modulate GABA(A) receptors via interactions at steroid binding sites.