3-hydroxy-3,4-dihydro-1,4-benzoxazepin-5(2H)-one | 877774-48-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 3-hydroxy-3,4-dihydro-1,4-benzoxazepin-5(2H)-one
• 英文别名: 3-hydroxy-3,4-dihydro-2H-1,4-benzoxazepin-5-one
• CAS: 877774-48-6
• 化学式: C₉H₉NO₃
• 分子量: 179.175
• InChiKey: MHGMEZRJEJSCSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-hydroxy-3,4-dihydro-1,4-benzoxazepin-5(2H)-one 在 甲基磺酰氯 、 三乙胺 作用下， 生成 1,4-benzoxazepin-5(2H)-one
  参考文献：
  名称：

  New 5-HT1A receptor agonists possessing 1,4-Benzoxazepine scaffold exhibit highly potent anti-ischemic effects

  摘要：

  A series of new 3-substituted-4-(4-aminobutyl)-1,4-benzoxazepin-5(4H)-one derivatives (1-5) which showed a very high affinity for 5-HT1A receptor with good selectivity over dopamine D-2 receptor was synthesized. Among these compounds, 3-chloro4-[4-[4-(2-pyridinyl)-1,2,3,6-tetrahydropyridin-1-yl]butyl]-1,4-benzoxazepin-5(4H)-one (5. SUN N4057) exhibited remarkable neuroprotective activity in a transient middle cerebral artery occlusion (t-MCAO) model. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00008-7
• 作为产物：
  描述：

  水杨酰胺 在 盐酸 、 potassium carbonate 作用下， 生成 3-hydroxy-3,4-dihydro-1,4-benzoxazepin-5(2H)-one
  参考文献：
  名称：

  New 5-HT1A receptor agonists possessing 1,4-Benzoxazepine scaffold exhibit highly potent anti-ischemic effects

  摘要：

  A series of new 3-substituted-4-(4-aminobutyl)-1,4-benzoxazepin-5(4H)-one derivatives (1-5) which showed a very high affinity for 5-HT1A receptor with good selectivity over dopamine D-2 receptor was synthesized. Among these compounds, 3-chloro4-[4-[4-(2-pyridinyl)-1,2,3,6-tetrahydropyridin-1-yl]butyl]-1,4-benzoxazepin-5(4H)-one (5. SUN N4057) exhibited remarkable neuroprotective activity in a transient middle cerebral artery occlusion (t-MCAO) model. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00008-7

文献信息

• Synthesis, SAR studies, and evaluation of 1,4-benzoxazepine derivatives as selective 5-HT1A receptor agonists with neuroprotective effect: Discovery of Piclozotan
  作者：Katsuhide Kamei、Noriko Maeda、Kayoko Nomura、Makoto Shibata、Ryoko Katsuragi-Ogino、Makoto Koyama、Mika Nakajima、Teruyoshi Inoue、Tomochika Ohno、Toshio Tatsuoka

  DOI：10.1016/j.bmc.2005.10.046

  日期：2006.3

  A new series of 1,4-benzoxazepine derivatives was designed, synthesized, and evaluated for binding to 5-HT1A receptor and cerebral anti-ischemic effect. A lot of compounds exhibited nanomolar affinity for 5-HT1A receptor with good selectivity over both dopamine D, and alpha(1)-adrenergic receptors. Among these compounds, 3-chloro-4-[4-[4-(2-pyridinyl)-1,2,3,6-tetrahydropyridin-1-y]butyl]-1, 4-benzoxazepin-5(4H)-one (50: SUN N4057 (Piclozotan) as 2HCl salt) showed remarkable neuroprotective activity in a transient middle cerebral artery occlusion (t-MCAO) model. (c) 2005 Elsevier Ltd. All rights reserved.
• New 5-HT1A receptor agonists possessing 1,4-Benzoxazepine scaffold exhibit highly potent anti-ischemic effects
  作者：Katsuhide Kamei、Noriko Maeda、Ryoko Ogino、Makoto Koyama、Mika Nakajima、Toshio Tatsuoka、Tomochika Ohno、Teruyoshi Inoue

  DOI：10.1016/s0960-894x(01)00008-7

  日期：2001.2

  A series of new 3-substituted-4-(4-aminobutyl)-1,4-benzoxazepin-5(4H)-one derivatives (1-5) which showed a very high affinity for 5-HT1A receptor with good selectivity over dopamine D-2 receptor was synthesized. Among these compounds, 3-chloro4-[4-[4-(2-pyridinyl)-1,2,3,6-tetrahydropyridin-1-yl]butyl]-1,4-benzoxazepin-5(4H)-one (5. SUN N4057) exhibited remarkable neuroprotective activity in a transient middle cerebral artery occlusion (t-MCAO) model. (C) 2001 Elsevier Science Ltd. All rights reserved.