(3α,5β,17β)-3-hydroxyandrostane-17-carbonitrile | 51872-52-7

• 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: (3α,5β,17β)-3-hydroxyandrostane-17-carbonitrile
• 英文别名: 3α-hydroxy-5β-androstane-17β-carbonitrile；17β-Cyano-3α-hydroxy-5β-androstane；(3alpha,5beta,17beta)-3-Hydroxyandrostane-17-carbonitrile；(3R,5R,8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carbonitrile
• CAS: 51872-52-7
• 化学式: C₂₀H₃₁NO
• 分子量: 301.472
• InChiKey: DVTDUTYENPZLFP-ULWYFIRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3α,5β,17β)-3-hydroxyandrostane-17-carbonitrile 在 sodium benzoate 、 sodium hydroxide 、 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 生成 (3β,5β,17β)-3-hydroxyandrostane-17-carbonitrile
  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：

  诺龙 在 palladium on activated charcoal 吡啶 、 chromium(VI) oxide 、 氢氧化钾 、 sodium hydroxide 、 samarium diiodide 、 硫酸 、 氢气 、 potassium tri-sec-butyl-borohydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 12.5h， 生成 (3α,5β,17β)-3-hydroxyandrostane-17-carbonitrile
  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

文献信息

• Chemical compounds
  申请人：——

  公开号：US03943124A1

  公开（公告）日：1976-03-09

  Steroids of the androstane series having a 3.alpha.-hydroxy group, a 3.beta.-hydrogen or methyl group; a 10-hydrogen atom or methyl group, an 11-oxo group or two hydrogen atoms at the 11-position, a 17.alpha.-hydrogen atom, and a group at the 17.beta.-position which is esterified carboxyl group, an N-mono or di-substituted carbamoyl group, a cyano group, a formyl group or an acetalised formyl group; and the 3.alpha.-esters thereof. The steroids possess anaesthetic properties.

  雄烯烷系列类固醇具有3.alpha.-羟基、3.beta.-氢或甲基基团；10-氢原子或甲基基团，11-位置处的11-酮基团或两个氢原子，17.alpha.-氢原子，以及17.beta.-位置上的羧酰化羧基团，N-单或双取代的氨基甲酰基团，氰基团，甲酰基团或乙缩甲酰基团；以及其3.alpha.-酯。这些类固醇具有麻醉性能。
• 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.