2,3-Dihydro-3-[4-[2-(2-hydroxyethoxy)ethyl]piperazino]-methyl-2,2,4,6,7-pentamethyl-1-benzofuran-5-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 2,3-Dihydro-3-[4-[2-(2-hydroxyethoxy)ethyl]piperazino]-methyl-2,2,4,6,7-pentamethyl-1-benzofuran-5-ol
• 英文别名: 3-[[4-[2-(2-hydroxyethoxy)ethyl]piperazin-1-yl]methyl]-2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-ol
• 化学式: C₂₂H₃₆N₂O₄
• 分子量: 392.539
• InChiKey: XEXAAIMYBATELA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  65.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  6-hydroxy-2,2,5,7,8-pentamethylchroman-4-one 在 吡啶 、 sodium hydroxide 、 thallium(III) nitrate trihydrate 、 dimethyl sulfide borane 、 bromotriphenylphosphonium bromide 、 碳酸氢钠 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 217.83h， 生成 2,3-Dihydro-3-[4-[2-(2-hydroxyethoxy)ethyl]piperazino]-methyl-2,2,4,6,7-pentamethyl-1-benzofuran-5-ol
  参考文献：
  名称：

  2,3-Dihydro-1-benzofuran-5-ols as Analogs of .alpha.-Tocopherol That Inhibit in Vitro and ex Vivo Lipid Autoxidation and Protect Mice against Central Nervous System Trauma

  摘要：

  A series of a-tocopherol analogues was synthesized with potential therapeutic value for such pathological conditions as stroke and trauma. A set of criteria such as the inhibition of in vitro lipid peroxidation, superoxyl radical scavenging, and brain penetration, as measured by ex vivo inhibition of lipid peroxidation, was applied to select the most effective compound. 2,3-Dihydro-2,2,4,6,7-pentamethyl-3-[(4-methylpiperazino)methyl]-1-benzofuran-5-ol hydrochloride (22) was selected because of its superior antioxidant properties and better brain penetration. This compound also protected mice against the effects of head injury. The criteria thus turned out to be useful for the characterization of a neuroprotective analogue of alpha-tocopherol.

  DOI：

  10.1021/jm00003a008

文献信息

• NOVEL DERIVATIVES OF 2,3-DIHYDRO-2,2,4,6,7-PENTAALKYL-5-BENZOFURANOLS
  申请人：MERRELL PHARMACEUTICALS INC.

  公开号：EP0635009B1

  公开（公告）日：1997-09-17
• 2,3-Dihydro-1-benzofuran-5-ols as Analogs of .alpha.-Tocopherol That Inhibit in Vitro and ex Vivo Lipid Autoxidation and Protect Mice against Central Nervous System Trauma
  作者：J. Martin Grisar、Frank N. Bolkenius、Margaret A. Petty、Joelle Verne

  DOI：10.1021/jm00003a008

  日期：1995.2

  A series of a-tocopherol analogues was synthesized with potential therapeutic value for such pathological conditions as stroke and trauma. A set of criteria such as the inhibition of in vitro lipid peroxidation, superoxyl radical scavenging, and brain penetration, as measured by ex vivo inhibition of lipid peroxidation, was applied to select the most effective compound. 2,3-Dihydro-2,2,4,6,7-pentamethyl-3-[(4-methylpiperazino)methyl]-1-benzofuran-5-ol hydrochloride (22) was selected because of its superior antioxidant properties and better brain penetration. This compound also protected mice against the effects of head injury. The criteria thus turned out to be useful for the characterization of a neuroprotective analogue of alpha-tocopherol.