(3α,4β,5α)-3-hydroxy-4-methoxyandrostan-16-one | 1516884-17-5

• 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,4β,5α)-3-hydroxy-4-methoxyandrostan-16-one
• 英文别名: (3R,4R,5R,8S,9S,10R,13R,14S)-3-hydroxy-4-methoxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,17-tetradecahydrocyclopenta[a]phenanthren-16-one
• CAS: 1516884-17-5
• 化学式: C₂₀H₃₂O₃
• 分子量: 320.472
• InChiKey: LFADNTSDZQEXPT-OFRYCBQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (3α,4β,17β)-3,17-dihydroxy-4-methoxyandrostan-16-one diacetate 在 samarium diiodide 、 水 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 生成 (3α,4β,5α)-3-hydroxy-4-methoxyandrostan-16-one
  参考文献：
  名称：

  Neurosteroid Analogues. 18. Structure–Activity Studies of ent-Steroid Potentiators of γ-Aminobutyric Acid Type A Receptors and Comparison of Their Activities with Those of Alphaxalone and Allopregnanolone

  摘要：

  A model of the alignment of neurosteroids and ent-neurosteroids at the same binding site on gamma-aminobutyric acid type A (GABA(A)) receptors was evaluated for its ability to identify the structural features in ent-neurosteroids that enhance their activity as positive allosteric modulators of this receptor. Structural features that were identified included: (1) a ketone group at position C-16, (2) an axial 4 alpha-OMe group, and (3) a C-18 methyl group. Two ent-steroids were identified that were more potent than the anesthetic steroid alphaxalone in their threshold for and duration of loss of the righting reflex in mice. In tadpoles, loss of righting reflex for these two ent-steroids 0 occurs with EC50 values similar to those found for allopregnanolone. The results indicate that ent-steroids have considerable potential to be developed as anesthetic agents and as drugs to treat brain disorders that are ameliorated by positive allosteric modulators of GABA(A) receptor function.

  DOI：

  10.1021/jm401577c

文献信息

• Neurosteroid Analogues. 18. Structure–Activity Studies of <i>ent</i>-Steroid Potentiators of γ-Aminobutyric Acid Type A Receptors and Comparison of Their Activities with Those of Alphaxalone and Allopregnanolone
  作者：Mingxing Qian、Kathiresan Krishnan、Eva Kudova、Ping Li、Brad D. Manion、Amanda Taylor、George Elias、Gustav Akk、Alex S. Evers、Charles F. Zorumski、Steven Mennerick、Douglas F. Covey

  DOI：10.1021/jm401577c

  日期：2014.1.9

  A model of the alignment of neurosteroids and ent-neurosteroids at the same binding site on gamma-aminobutyric acid type A (GABA(A)) receptors was evaluated for its ability to identify the structural features in ent-neurosteroids that enhance their activity as positive allosteric modulators of this receptor. Structural features that were identified included: (1) a ketone group at position C-16, (2) an axial 4 alpha-OMe group, and (3) a C-18 methyl group. Two ent-steroids were identified that were more potent than the anesthetic steroid alphaxalone in their threshold for and duration of loss of the righting reflex in mice. In tadpoles, loss of righting reflex for these two ent-steroids 0 occurs with EC50 values similar to those found for allopregnanolone. The results indicate that ent-steroids have considerable potential to be developed as anesthetic agents and as drugs to treat brain disorders that are ameliorated by positive allosteric modulators of GABA(A) receptor function.