(3α,5α)-3-hydroxy-11-oxoandrost-16-ene-17-carbonitrile | 1258041-13-2

• 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,5α)-3-hydroxy-11-oxoandrost-16-ene-17-carbonitrile
• 英文别名: (3R,5S,8S,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-11-oxo-1,2,3,4,5,6,7,8,9,12,14,15-dodecahydrocyclopenta[a]phenanthrene-17-carbonitrile
• CAS: 1258041-13-2
• 化学式: C₂₀H₂₇NO₂
• 分子量: 313.44
• InChiKey: NQFWHWPKEITVRR-WTJPMNHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3α,5α)-3-hydroxy-11-oxoandrost-16-ene-17-carbonitrile 在 5% Pd(II)/C(eggshell) 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 以30 mg的产率得到(3α,5α,17β)-3-hydroxy-11-oxoandrostane-17-carbonitrile
  参考文献：
  名称：

  Neurosteroid analogues. 15. A comparative study of the anesthetic and GABAergic actions of alphaxalone, Δ16-alphaxalone and their corresponding 17-carbonitrile analogues

  摘要：

  Alphaxalone, a neuroactive steroid containing a 17 beta-acetyl group, has potent anesthetic activity in humans. This pharmacological activity is attributed to this steroid's enhancement of gamma-amino butyric acid-mediated chloride currents at gamma-amino butyric acid type A receptors. The conversion of alphaxalone into Delta(16)-alphaxalone produces an analogue that lacks anesthetic activity in humans and that has greatly diminished receptor actions. By contrast, the corresponding 17 beta-carbonitrile analogue of alphaxalone and the Delta(16)-17-carbonitrile analogue both have potent anesthetic and receptor actions. The differential effect of the Delta(16)-double bond on the actions of alphaxalone and the 17 beta-carbonitrile analogue is accounted for by a differential effect on the orientation of the 17-acetyl and 17-carbonitrile substituents. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.008
• 作为产物：
  描述：

  (3α,5α)-3-(methyloxymethyl)oxy-11-oxoandrost-16-ene-17-carbonitrile 在 盐酸 、 水 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 以93%的产率得到(3α,5α)-3-hydroxy-11-oxoandrost-16-ene-17-carbonitrile
  参考文献：
  名称：

  Neurosteroid analogues. 15. A comparative study of the anesthetic and GABAergic actions of alphaxalone, Δ16-alphaxalone and their corresponding 17-carbonitrile analogues

  摘要：

  Alphaxalone, a neuroactive steroid containing a 17 beta-acetyl group, has potent anesthetic activity in humans. This pharmacological activity is attributed to this steroid's enhancement of gamma-amino butyric acid-mediated chloride currents at gamma-amino butyric acid type A receptors. The conversion of alphaxalone into Delta(16)-alphaxalone produces an analogue that lacks anesthetic activity in humans and that has greatly diminished receptor actions. By contrast, the corresponding 17 beta-carbonitrile analogue of alphaxalone and the Delta(16)-17-carbonitrile analogue both have potent anesthetic and receptor actions. The differential effect of the Delta(16)-double bond on the actions of alphaxalone and the 17 beta-carbonitrile analogue is accounted for by a differential effect on the orientation of the 17-acetyl and 17-carbonitrile substituents. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.008

文献信息

• NEUROACTIVE 17(20)-Z-VINYLCYANO-SUBSTITUTED STEROIDS, PRODRUGS THEREOF, AND METHODS OF TREATMENT USING SAME
  申请人：Covey Douglas

  公开号：US20140309443A1

  公开（公告）日：2014-10-16

  The present disclosure is generally directed to neuroactive 17(20)-Z-vinylcyano-substituted compound of Formula (I) and (II), as referenced herein, and pharmaceutically acceptable salts thereof, for use as, for example, an anesthetic, and/or in the treatment of disorders relating to GABA function and activity. The present disclosure is further directed to pharmaceutical compositions comprising such compounds.

  本公开涉及一般指向化合物的神经活性17(20)-Z-乙烯基氰基取代物，其化学式为(I)和(II)，并且其药学上可接受的盐，例如用作麻醉剂，和/或用于治疗与GABA功能和活性相关的疾病。本公开还涉及包含这种化合物的药物组合物。
• US9388210B2
  申请人：——

  公开号：US9388210B2

  公开（公告）日：2016-07-12
• Neurosteroid analogues. 15. A comparative study of the anesthetic and GABAergic actions of alphaxalone, Δ16-alphaxalone and their corresponding 17-carbonitrile analogues
  作者：Achintya K. Bandyopadhyaya、Brad D. Manion、Ann Benz、Amanda Taylor、Nigam P. Rath、Alex S. Evers、Charles F. Zorumski、Steven Mennerick、Douglas F. Covey

  DOI：10.1016/j.bmcl.2010.09.008

  日期：2010.11

  Alphaxalone, a neuroactive steroid containing a 17 beta-acetyl group, has potent anesthetic activity in humans. This pharmacological activity is attributed to this steroid's enhancement of gamma-amino butyric acid-mediated chloride currents at gamma-amino butyric acid type A receptors. The conversion of alphaxalone into Delta(16)-alphaxalone produces an analogue that lacks anesthetic activity in humans and that has greatly diminished receptor actions. By contrast, the corresponding 17 beta-carbonitrile analogue of alphaxalone and the Delta(16)-17-carbonitrile analogue both have potent anesthetic and receptor actions. The differential effect of the Delta(16)-double bond on the actions of alphaxalone and the 17 beta-carbonitrile analogue is accounted for by a differential effect on the orientation of the 17-acetyl and 17-carbonitrile substituents. (C) 2010 Elsevier Ltd. All rights reserved.