ent-(5β)-androstane-3,17-dione | 960525-62-6

• 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: ent-(5β)-androstane-3,17-dione
• 英文别名: (5S,8S,9R,10R,13R,14R)-10,13-dimethyl-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthrene-3,17-dione
• CAS: 960525-62-6
• 化学式: C₁₉H₂₈O₂
• 分子量: 288.43
• InChiKey: RAJWOBJTTGJROA-ZPVXQFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ent-(5β)-androstane-3,17-dione 在 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以90%的产率得到ent-etiocholanolone
  参考文献：
  名称：

  Neurosteroid analogues. 12. Potent enhancement of GABA-mediated chloride currents at GABAA receptors by ent-androgens

  摘要：

  Allopregnanolone (1) and pregnanolone (2), steroids containing a 17 beta-acetyl group, are potent enhancers of GABA (gamma-aminobutyric acid) action at GABA(A) receptors. Their effects are enantioselective with the non-naturally occurring enantiomers (ent-1 and ent-2) being less potent. Androsterone (3) and etiocholanolone (4), steroids with a C-17 carbonyl group, are weak enhancers of GABA action at GABA(A) receptors. Unexpectedly, their enantiomers (ent-3 and ent-4) have been found to have enhanced, not diminished, activity at GABA(A) receptors. Furthermore, the C-17 spiro-epoxide analogues (ent-5 and ent-6) of ent-3 and ent-4, respectively, have activities comparable to those of steroids 1 and 2. The results indicate that some ent-steroids are potent modulators of GABA(A) receptors and might have clinical potential as GABAergic drugs of the future. (C) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.02.017
• 作为产物：
  描述：

  ent-(5β,17β)-17-hydroxyandrostan-3-one 在 jones reagent 作用下， 以 丙酮 为溶剂， 反应 0.5h， 以93%的产率得到ent-(5β)-androstane-3,17-dione
  参考文献：
  名称：

  Neurosteroid analogues. 12. Potent enhancement of GABA-mediated chloride currents at GABAA receptors by ent-androgens

  摘要：

  Allopregnanolone (1) and pregnanolone (2), steroids containing a 17 beta-acetyl group, are potent enhancers of GABA (gamma-aminobutyric acid) action at GABA(A) receptors. Their effects are enantioselective with the non-naturally occurring enantiomers (ent-1 and ent-2) being less potent. Androsterone (3) and etiocholanolone (4), steroids with a C-17 carbonyl group, are weak enhancers of GABA action at GABA(A) receptors. Unexpectedly, their enantiomers (ent-3 and ent-4) have been found to have enhanced, not diminished, activity at GABA(A) receptors. Furthermore, the C-17 spiro-epoxide analogues (ent-5 and ent-6) of ent-3 and ent-4, respectively, have activities comparable to those of steroids 1 and 2. The results indicate that some ent-steroids are potent modulators of GABA(A) receptors and might have clinical potential as GABAergic drugs of the future. (C) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.02.017

文献信息

• Neurosteroid analogues. 12. Potent enhancement of GABA-mediated chloride currents at GABAA receptors by ent-androgens
  作者：Bryson W. Katona、Kathiresan Krishnan、Zu Yun Cai、Brad D. Manion、Ann Benz、Amanda Taylor、Alex S. Evers、Charles F. Zorumski、Steven Mennerick、Douglas F. Covey

  DOI：10.1016/j.ejmech.2007.02.017

  日期：2008.1

  Allopregnanolone (1) and pregnanolone (2), steroids containing a 17 beta-acetyl group, are potent enhancers of GABA (gamma-aminobutyric acid) action at GABA(A) receptors. Their effects are enantioselective with the non-naturally occurring enantiomers (ent-1 and ent-2) being less potent. Androsterone (3) and etiocholanolone (4), steroids with a C-17 carbonyl group, are weak enhancers of GABA action at GABA(A) receptors. Unexpectedly, their enantiomers (ent-3 and ent-4) have been found to have enhanced, not diminished, activity at GABA(A) receptors. Furthermore, the C-17 spiro-epoxide analogues (ent-5 and ent-6) of ent-3 and ent-4, respectively, have activities comparable to those of steroids 1 and 2. The results indicate that some ent-steroids are potent modulators of GABA(A) receptors and might have clinical potential as GABAergic drugs of the future. (C) 2007 Elsevier Masson SAS. All rights reserved.