3α-hydroxy-5β-pregnan-20-one L-valine ester | 1185296-00-7

• 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-hydroxy-5β-pregnan-20-one L-valine ester
• 英文别名: 3α-L-valine-5β-pregnane-20-one；L-Valine, (3I+/-,5I(2))-20-oxopregnan-3-yl ester；[(3R,5R,8R,9S,10S,13S,14S,17S)-17-acetyl-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] (2S)-2-amino-3-methylbutanoate
• CAS: 1185296-00-7
• 化学式: C₂₆H₄₃NO₃
• 分子量: 417.632
• InChiKey: LMHKDOXVMXUVGN-BVINDDIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  69.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3α-hydroxy-5β-pregnan-20-one L-valine ester 在 盐酸 作用下， 以 乙醚 为溶剂， 以71%的产率得到3α-hydroxy-5β-pregnan-20-one L-valine ester hydrochloride
  参考文献：
  名称：

  Development and Screening of Water-Soluble Analogues of Progesterone and Allopregnanolone in Models of Brain Injury

  摘要：

  Preclinical and clinical research findings have revealed that the hormone progesterone, when acutely administered, can dramatically reduce cerebral edema, inflammation, tissue necrosis, and programmed cell death following traumatic brain injury (TBI). The poor aqueous solubility of progesterone, however, limits its potential use as a therapeutic. Several chemically novel analogues of progesterone and its natural metabolite allopregnanolone have been synthesized and screened using both in vitro and whole animal models of TBI. The new derivatives demonstrated greatly improved solubility and select compounds have shown equivalent effectiveness to progesterone in reducing cerebral edema after TBI.

  DOI：

  10.1021/jm900712n
• 作为产物：
  描述：

  孕烷醇酮 在 哌啶 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 24.5h， 生成 3α-hydroxy-5β-pregnan-20-one L-valine ester
  参考文献：
  名称：

  [EN] STEROID ANALOGUES FOR NEUROPROTECTION
  [FR] ANALOGUES STÉROÏDIENS UTILISÉS EN NEUROPROTECTION

  摘要：

  公开号：

  WO2009108804A3

文献信息

• Development and Screening of Water-Soluble Analogues of Progesterone and Allopregnanolone in Models of Brain Injury
  作者：Christopher J. MacNevin、Fahim Atif、Iqbal Sayeed、Donald G. Stein、Dennis C. Liotta

  DOI：10.1021/jm900712n

  日期：2009.10.8

  Preclinical and clinical research findings have revealed that the hormone progesterone, when acutely administered, can dramatically reduce cerebral edema, inflammation, tissue necrosis, and programmed cell death following traumatic brain injury (TBI). The poor aqueous solubility of progesterone, however, limits its potential use as a therapeutic. Several chemically novel analogues of progesterone and its natural metabolite allopregnanolone have been synthesized and screened using both in vitro and whole animal models of TBI. The new derivatives demonstrated greatly improved solubility and select compounds have shown equivalent effectiveness to progesterone in reducing cerebral edema after TBI.
• [EN] STEROID ANALOGUES FOR NEUROPROTECTION<br/>[FR] ANALOGUES STÉROÏDIENS UTILISÉS EN NEUROPROTECTION
  申请人：UNIV EMORY

  公开号：WO2009108804A3

  公开（公告）日：2009-12-10