4-(4-bromobutyl)-1,2-dihydro-4H-1,4-benzodiazepine-3,5-dione | 137133-39-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: 4-(4-bromobutyl)-1,2-dihydro-4H-1,4-benzodiazepine-3,5-dione
• 英文别名: 4-(4-bromobutyl)-2,3,4,5-tetrahydro-1,4-benzodiazepine-3,5-dione；4-(4-Bromobutyl)-2,3,4,5-tetrahydro-1,4-benzodiazepine-3.5-dione；4-(4-bromobutyl)-1,2-dihydro-1,4-benzodiazepine-3,5-dione
• CAS: 137133-39-2
• 化学式: C₁₃H₁₅BrN₂O₂
• 分子量: 311.178
• InChiKey: VODPIHRSSWBXRB-UHFFFAOYSA-N

物化性质

• 熔点：
  60-61 °C
• 沸点：
  491.4±45.0 °C(Predicted)
• 密度：
  1.428±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-bromobutyl)-1,2-dihydro-4H-1,4-benzodiazepine-3,5-dione 、 1-(2-嘧啶基)哌嗪 以 1,4-二氧六环 为溶剂， 反应 8.0h， 以to obtain 77.0 mg of the desired compound (yield 87%)的产率得到4-[4-[4-(2-pyrimidinyl)piperazin-1-yl]butyl]-1,2-dihydro-4H-1,4-benzodiazepine-3,5-dione
  参考文献：
  名称：

  Fused 7-membered cyclic compound and antipsychotic preparation

  摘要：

  一种治疗涉及血清素通路疾病的疗效良好的抗精神病制剂，包括具有公式（I）或其盐的融合环化合物： ##STR1## 其中A和B均为羰基基团，或者一个表示亚甲基基团，另一个表示羰基基团，Z表示硫原子，或者可被取代的氮原子或亚甲基基团，R表示芳香或杂环基团，可被取代，X表示氢原子、卤原子、C.sub.1-C.sub.5低碳基、C.sub.1-C.sub.5低烷氧基、C.sub.7-C.sub.9芳基烷氧基、C.sub.1-C.sub.5低酰氧基、C.sub.7-C.sub.10芳基羰基氧基、羟基、硝基或酯基，n为2至10的整数。

  公开号：

  US05312625A1
• 作为产物：
  描述：

  1,4-二溴丁烷 、 2,3,4,5-tetrahydro-1,4-benzodiazepine-3,5-dione 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以64%的产率得到4-(4-bromobutyl)-1,2-dihydro-4H-1,4-benzodiazepine-3,5-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

• Fused 7-membered cyclic compound and antipsychotic preparation
  申请人：Suntory Limited

  公开号：US05312625A1

  公开（公告）日：1994-05-17

  A therapeutically effective antipsychotic preparation comprising a fused cyclic compound for the treatment of diseases involving the serotonergic pathway having the formula (I) or salts thereof: ##STR1## wherein both of A and B are carbonyl groups, or one represents a methylene group and the other a carbonyl group, Z represents a sulfur atom, or a nitrogen atom which may be substituted, or a methylene group, R represents an aromatic or heterocylcic 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 C.sub.1 -C.sub.5 lower acyloxy group, a C.sub.7 -C.sub.10 arylcarbonyloxy group, a hydroxy group, a nitro group or an ester group, and n is an integer of 2 to 10.

  一种治疗涉及血清素通路疾病的疗效良好的抗精神病制剂，包括具有公式（I）或其盐的融合环化合物： ##STR1## 其中A和B均为羰基基团，或者一个表示亚甲基基团，另一个表示羰基基团，Z表示硫原子，或者可被取代的氮原子或亚甲基基团，R表示芳香或杂环基团，可被取代，X表示氢原子、卤原子、C.sub.1-C.sub.5低碳基、C.sub.1-C.sub.5低烷氧基、C.sub.7-C.sub.9芳基烷氧基、C.sub.1-C.sub.5低酰氧基、C.sub.7-C.sub.10芳基羰基氧基、羟基、硝基或酯基，n为2至10的整数。
• Heterocyclic compound and psychopharmaceutical composition containing same
  申请人：SUNTORY LIMITED

  公开号：EP0463810A1

  公开（公告）日：1992-01-02

  A condensed heterocyclic compound having the formula (I): wherein A and B are both carbonyl groups or one thereof represents a methylene group and the other represents a carbonyl group; Z represents an oxygen atom, a sulfur atom, a substituted or unsubstituted nitrogen atom, or a methylene group; n is an integer of 2 to 6; and R represents a group having the following formula: wherein R¹ represents a hydrogen atom or a hydroxyl group; R² represents a substituted or unsubstituted phenyl or 2-pyridyl group or salts thereof. The compounds exhibit a strong affinity to the σ-receptor and are useful as psychopharmaceuticals.

  具有式 (I) 的缩合杂环化合物： 其中 A 和 B 都是羰基，或其中一个代表亚甲基，另一个代表羰基；Z 代表氧原子、硫原子、取代或未取代的氮原子或亚甲基；n 是 2 到 6 的整数；R 代表具有下式的基团： 其中 R¹ 代表氢原子或羟基；R² 代表取代或未取代的苯基或 2-吡啶基或其盐类。 这些化合物对 σ 受体有很强的亲和力，可用作精神药物。
• Fused 7-membered cyclic compound and antipsychotic preparation containing the same
  申请人：SUNTORY LIMITED

  公开号：EP0444924B1

  公开（公告）日：1996-01-03
• US5312625A
  申请人：——

  公开号：US5312625A

  公开（公告）日：1994-05-17
• 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.