4-[4-[4-(2-pyrimidinyl)piperazin-1-yl]butyl]-1,4-benzoxazepine-3,5(2H,4H)-dione | 131112-58-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 4-[4-[4-(2-pyrimidinyl)piperazin-1-yl]butyl]-1,4-benzoxazepine-3,5(2H,4H)-dione
• 英文别名: 4-(4-(4-(2-Pyrimidyl)-1-piperazinyl)butyl)-1,4-benzoxazepine-3,5(2H,4H)-dione；4-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]-1,4-benzoxazepine-3,5-dione
• CAS: 131112-58-8
• 化学式: C₂₁H₂₅N₅O₃
• 分子量: 395.461
• InChiKey: ITTHDTFPCPHJOU-UHFFFAOYSA-N

物化性质

• 熔点：
  145-147 °C(Solv: methanol (67-56-1); ethyl ether (60-29-7))
• 沸点：
  634.6±65.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  水杨酰胺 在 sodium methylate 、 sodium hydride 、 potassium carbonate 、 sodium iodide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 反应 8.0h， 生成 4-[4-[4-(2-pyrimidinyl)piperazin-1-yl]butyl]-1,4-benzoxazepine-3,5(2H,4H)-dione
  参考文献：
  名称：

  Synthesis, SAR studies, and evaluation of 1,4-benzoxazepine derivatives as selective 5-HT1A receptor agonists with neuroprotective effect: Discovery of Piclozotan

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2005.10.046

文献信息

• Benzoxazepine derivative
  申请人：Suntory Limited

  公开号：US05071845A1

  公开（公告）日：1991-12-10

  A benzoxazepine derivative suitable for use as a psychotropic composition having the formula: ##STR1## wherein A and B are both carbonyl groups, or one thereof represents a methylene group and the other a carbonyl group, R represents an aromatic group or a heterocyclic group, which may be substituted, X represents a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.5 lower alkyl group, a C.sub.1 -c.sub.5 lower alkoxy group, a C.sub.7 -C.sub.9 arylalkoxy group, a hydroxyl group, a nitro group, or an ester group, and n is an integer of 2 to 10 and salts thereof.

  适用作为精神药物组合物的苯并噁唑啶衍生物，其化学式为：##STR1## 其中A和B均为羰基基团，或其中之一表示亚甲基基团，另一个表示羰基基团，R表示芳香基团或杂环基团，可以被取代，X表示氢原子，卤原子，C.sub.1-C.sub.5低烷基基团，C.sub.1-C.sub.5低烷氧基团，C.sub.7-C.sub.9芳基烷氧基团，羟基，硝基或酯基，n为2到10的整数及其盐。
• Benzoxazepine derivatives
  申请人：SUNTORY LIMITED

  公开号：EP0376633A2

  公开（公告）日：1990-07-04

  A benzoxazepine derivative suitable for use as a psychotropic composition having the formula: wherein A and B are both carbonyl groups, or one thereof represents a methylene group and the other a carbonyl group, R represents an aromatic group or a heterocyclic group, which may be substituted, X represents a hydrogen atom, a halogen atom, a Ci - C5 lower alkyl group, a C1- Cs lower alkoxy group, a C7 - C9 arylalkoxy group, a hydroxyl group, a nitro group, or an ester group, and n is an integer of 2 to 10, or a salt thereof.

  一种适合用作精神药物的苯并氧氮杂卓衍生物，其式如下 其中 A 和 B 均为羰基，或其中一个代表亚甲基，另一个代表羰基，R 代表芳香基团或杂环基团，可被取代，X 代表氢原子、卤素原子、Ci-C5 低级烷基、C1-Cs 低级烷氧基、C7-C9 芳基烷氧基、羟基、硝基或酯基，n 为 2-10 的整数，或其盐。
• 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.