1-((1S,3aS,3bS,7R,10aR,10bS,12aS)-7-hydroxy-10a,12a-dimethyl-1,2,3,3a,3b,4,6,7,8,9,10,10a,10b,11,12,12a-hexadecahydrocyclohepta[a]cyclopenta[f]naphthalen-1-yl)ethan-1-one | 1234504-09-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-((1S,3aS,3bS,7R,10aR,10bS,12aS)-7-hydroxy-10a,12a-dimethyl-1,2,3,3a,3b,4,6,7,8,9,10,10a,10b,11,12,12a-hexadecahydrocyclohepta[a]cyclopenta[f]naphthalen-1-yl)ethan-1-one
• 英文别名: 4α-hydroxy-A-homo-5-pregnen-20-one；1-[(1S,2R,6R,11S,12S,15S,16S)-6-hydroxy-2,16-dimethyl-15-tetracyclo[9.7.0.02,8.012,16]octadec-8-enyl]ethanone
• CAS: 1234504-09-6
• 化学式: C₂₂H₃₄O₂
• 分子量: 330.511
• InChiKey: CCORKEHGMREVMF-MVSFUWRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-((1S,3aS,3bS,7R,10aR,10bS,12aS)-7-hydroxy-10a,12a-dimethyl-1,2,3,3a,3b,4,6,7,8,9,10,10a,10b,11,12,12a-hexadecahydrocyclohepta[a]cyclopenta[f]naphthalen-1-yl)ethan-1-one 在 10 wt% Pd(OH)2 on carbon 、 氢气 作用下， 以 四氢呋喃 为溶剂， 50.0 ℃ 、344.75 kPa 条件下， 反应 16.0h， 以33%的产率得到1-((1S,3aS,3bR,5aS,7R,10aS,10bS,12aS)-7-hydroxy-10a,12a-dimethyloctadecahydrocyclohepta[a]cyclopenta[f]naphthalen-1-yl)ethan-1-one
  参考文献：
  名称：

  [EN] COMPOSITIONS AND METHODS FOR TREATING CNS DISORDERS
  [FR] COMPOSITIONS ET MÉTHODES PERMETTANT DE TRAITER LES TROUBLES DU SNC

  摘要：

  本文提供了一种式（I-I）的化合物或其药用可接受盐，其中t、R7、R3、R9、R6a、R6b、R11a、R11b、R15a、R15b、R16a、R16b、R17a、R17b、R18a、R18b、R19a、R19b、R5a、R5b、R8和R13在此定义。本文还提供了包括式（I-I）化合物的药物组合物以及使用这些化合物的方法，例如在治疗与中枢神经系统相关的疾病中。

  公开号：

  WO2019126761A1
• 作为产物：
  描述：

  pregn-5-ene-3,20-dione cyclic 20-(1,2-ethanediylacetal) 在 盐酸 、 potassium tri-sec-butyl-borohydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 36.0h， 生成 1-((1S,3aS,3bS,7R,10aR,10bS,12aS)-7-hydroxy-10a,12a-dimethyl-1,2,3,3a,3b,4,6,7,8,9,10,10a,10b,11,12,12a-hexadecahydrocyclohepta[a]cyclopenta[f]naphthalen-1-yl)ethan-1-one
  参考文献：
  名称：

  [EN] COMPOSITIONS AND METHODS FOR TREATING CNS DISORDERS
  [FR] COMPOSITIONS ET MÉTHODES PERMETTANT DE TRAITER LES TROUBLES DU SNC

  摘要：

  本文提供了一种式（I-I）的化合物或其药用可接受盐，其中t、R7、R3、R9、R6a、R6b、R11a、R11b、R15a、R15b、R16a、R16b、R17a、R17b、R18a、R18b、R19a、R19b、R5a、R5b、R8和R13在此定义。本文还提供了包括式（I-I）化合物的药物组合物以及使用这些化合物的方法，例如在治疗与中枢神经系统相关的疾病中。

  公开号：

  WO2019126761A1

文献信息

• Synthesis and GABAA receptor activity of A-homo analogues of neuroactive steroids
  作者：María V. Dansey、Pablo H. Di Chenna、Adriana S. Veleiro、Zdena Krištofíková、Hana Chodounska、Alexander Kasal、Gerardo Burton

  DOI：10.1016/j.ejmech.2010.03.037

  日期：2010.7

  A procedure is described for the preparation of A-homo-5-pregnenes via an acid catalyzed rearrangement of cyclopropylcarbinols assisted by microwave irradiation. 3 alpha-Hydroxy and 4 alpha-hydroxy-A-homo-5-pregnen-20-one, analogues of the neuroactive steroid allopregnanolone, were obtained by means of a regioselective epoxidation of a double bond in the expanded A-ring, using a fructose-derived chiral ketone as catalyst and oxone as oxidant. Although both these compounds were marginally active in inhibiting TBPS binding to GABA(A) receptors, 3 beta-hydroxy-A-homo-5-pregnen-20-one was almost as active as allopregnanolone. Reduction of the double bond of the latter compound resulted in a ten fold loss of activity. (c) 2010 Elsevier Masson SAS. All rights reserved.
• [EN] COMPOSITIONS AND METHODS FOR TREATING CNS DISORDERS<br/>[FR] COMPOSITIONS ET MÉTHODES PERMETTANT DE TRAITER LES TROUBLES DU SNC
  申请人：SAGE THERAPEUTICS INC

  公开号：WO2019126761A1

  公开（公告）日：2019-06-27

  Provided herein is a compound of Formula (I-I) or a pharmaceutically acceptable salt thereof, wherein t, R7, R3, R9, R6a, R6b, R11a, R11b, R15a, R15b, R16a, R16b, R17a, R17b, R18a, R18b, R19a, R19b, R5a, R5b, R8 and R13 are defined herein. Also provided herein are pharmaceutical compositions comprising a compound of Formula (I-I) and methods of using the compounds, e.g., in the treatment of CNS-related disorders.

  本文提供了一种式（I-I）的化合物或其药用可接受盐，其中t、R7、R3、R9、R6a、R6b、R11a、R11b、R15a、R15b、R16a、R16b、R17a、R17b、R18a、R18b、R19a、R19b、R5a、R5b、R8和R13在此定义。本文还提供了包括式（I-I）化合物的药物组合物以及使用这些化合物的方法，例如在治疗与中枢神经系统相关的疾病中。