3,20-hydroxy-progesterone

• 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: 3,20-hydroxy-progesterone
• 英文别名: (8S,9S,10R,13S,14S,17S)-17-[(1R)-1-hydroxyethyl]-10,13-dimethyl-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
• 化学式: C₂₁H₃₄O₂
• 分子量: 318.5
• InChiKey: IBMZAHKIAAJREF-OYSRNKDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,20-hydroxy-progesterone 在 chromium(VI) oxide 、 硫酸 、 碘 、 铜 、 锌 作用下， 以 丙酮 为溶剂， 反应 0.5h， 生成 (8S,9S,10R,13S,14S,17S)-17-Acetyl-10,13-dimethyl-hexadecahydro-cyclopropa[4,5]cyclopenta[a]phenanthren-3-one
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jm960304p
• 作为产物：
  描述：

  黄体酮 在 lithium aluminium tetrahydride 、 水 、 sodium sulfate 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 1.5h， 以80%的产率得到
  参考文献：
  名称：

  [EN] STEROID ANALOGUES FOR NEUROPROTECTION
  [FR] ANALOGUES STÉROÏDIENS UTILISÉS EN NEUROPROTECTION

  摘要：

  公开号：

  WO2009108804A3

文献信息

• [EN] STEROID ANALOGUES FOR NEUROPROTECTION<br/>[FR] ANALOGUES STÉROÏDIENS UTILISÉS EN NEUROPROTECTION
  申请人：UNIV EMORY

  公开号：WO2009108804A3

  公开（公告）日：2009-12-10
• 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.