methyl 2,3-dihydro-5-<(4-nitrobenzoyl)oxy>-2,2,4,6,7-pentamethyl-1-benzofuran-3-carboxylate | 161528-14-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2,3-dihydro-5-<(4-nitrobenzoyl)oxy>-2,2,4,6,7-pentamethyl-1-benzofuran-3-carboxylate
• 英文别名: 2,3-dihydro-5-(4-nitrobenzoyl)oxy-2,2,4,6,7-pentamethyl-1-benzofuran-3-carboxylic acid, methyl ester；2,3-dihydro-5-(4-nitrobenzoyl)oxy-2,2,4,6,7-pentamethyl-1-benzofuran-3-carboxylic acid,methyl ester；methyl 2,2,4,6,7-pentamethyl-5-(4-nitrobenzoyl)oxy-3H-1-benzofuran-3-carboxylate
• CAS: 161528-14-9
• 化学式: C₂₂H₂₃NO₇
• 分子量: 413.427
• InChiKey: VWWZVRBCEGSYOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2,3-dihydro-5-<(4-nitrobenzoyl)oxy>-2,2,4,6,7-pentamethyl-1-benzofuran-3-carboxylate 在 吡啶 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 48.83h， 生成 5-acetoxy-2,3-dihydro-2,2,4,6,7-pentamethyl-1-benzofuran-3-carboxylic acid
  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
• 作为产物：
  描述：

  6-hydroxy-2,2,5,7,8-pentamethylchroman-4-one 在 吡啶 、 thallium(III) nitrate trihydrate 作用下， 以 甲醇 为溶剂， 反应 96.0h， 生成 methyl 2,3-dihydro-5-<(4-nitrobenzoyl)oxy>-2,2,4,6,7-pentamethyl-1-benzofuran-3-carboxylate
  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

• Derivatives of 2,3-dihydro benzofuranols
  申请人：Merrell Pharmaceuticals Inc.

  公开号：US05721233A1

  公开（公告）日：1998-02-24

  Derivatives of 2,3-dihydro-5-benzofuranol, intermediates thereof, and processes useful for their preparation. These compounds are free radical scavengers and are useful in the treatment of conditions capable of being treated by free radical scavengers, such as stroke, nervous system trauma and reperfusion damage.

  2,3-二氢-5-苯并呋喃醇的衍生物，其中间体以及用于它们制备的有用过程。这些化合物是自由基清除剂，在治疗能够通过自由基清除剂治疗的疾病，如中风、神经系统创伤和再灌注损伤方面具有用处。
• 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.