3-{4-[4-(3-chlorophenyl)piperazin-1-yl]butyl}-8-phenyl-1,3-diazaspiro[4,5]decan-2,4-dione

• 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: 3-{4-[4-(3-chlorophenyl)piperazin-1-yl]butyl}-8-phenyl-1,3-diazaspiro[4,5]decan-2,4-dione
• 英文别名: 3-[4-[4-(3-Chlorophenyl)piperazin-1-yl]butyl]-8-phenyl-1,3-diazaspiro[4.5]decane-2,4-dione；3-[4-[4-(3-chlorophenyl)piperazin-1-yl]butyl]-8-phenyl-1,3-diazaspiro[4.5]decane-2,4-dione
• 化学式: C₂₈H₃₅ClN₄O₂
• 分子量: 495.065
• InChiKey: QJGIKEDKMVPCFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-{4-[4-(3-chlorophenyl)piperazin-1-yl]butyl}-8-phenyl-1,3-diazaspiro[4,5]decan-2,4-dione 在 盐酸 作用下， 以 乙醇 为溶剂， 生成 3-{4-[4-(3-chlorophenyl)piperazin-1-yl]butyl}-8-phenyl-1,3-diazaspiro[4,5]decan-2,4-dione hydrochloride
  参考文献：
  名称：

  Novel spirohydantoin derivative as a potent multireceptor-active antipsychotic and antidepressant agent

  摘要：

  A series of novel spirohydantoin derivatives with arylpiperazinylbutyl moiety were synthesized and evaluated for serotonin 5-HT1A, 5-HT2A, 5-HT7 and dopamine D-2 receptors. Based on these data, four compounds were selected for further binding affinity assays on dopamine D-1, D-3, D-4, and 5-HT2C, 5-HT6 as well as adrenergic alpha 1 and alpha(2C) receptors, which are involved in various CNS diseases such as schizophrenia, anxiety and/or depression. The compound 14, 1-{4-[4-(2-metoxyphe-nyl) piperazin-1-yl] butyl}-3',4'-dihydro-2H, 2'H, 5H-spiro[imidazolidine-4,1'-naphthalene]-2,5-dione, with the most promising functional profile, mixed 5-HT2A/D-2 antagonist and 5-HT1A partial agonist, was selected. In the mouse D-amphetamine-induced locomotor hyperactivity model, compound 14 produced antipsychotic-like activity, which is devoid of cataleptogenic effects and in the forced swim test in mice, it showed a significant antidepressant-like effect unlike the reference drug aripiprazole. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.04.026
• 作为产物：
  描述：

  8-苯基-1,3-二氮杂螺[4.5]癸烷-2,4-二酮 在 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 、 乙腈 为溶剂， 生成 3-{4-[4-(3-chlorophenyl)piperazin-1-yl]butyl}-8-phenyl-1,3-diazaspiro[4,5]decan-2,4-dione
  参考文献：
  名称：

  Novel spirohydantoin derivative as a potent multireceptor-active antipsychotic and antidepressant agent

  摘要：

  A series of novel spirohydantoin derivatives with arylpiperazinylbutyl moiety were synthesized and evaluated for serotonin 5-HT1A, 5-HT2A, 5-HT7 and dopamine D-2 receptors. Based on these data, four compounds were selected for further binding affinity assays on dopamine D-1, D-3, D-4, and 5-HT2C, 5-HT6 as well as adrenergic alpha 1 and alpha(2C) receptors, which are involved in various CNS diseases such as schizophrenia, anxiety and/or depression. The compound 14, 1-{4-[4-(2-metoxyphe-nyl) piperazin-1-yl] butyl}-3',4'-dihydro-2H, 2'H, 5H-spiro[imidazolidine-4,1'-naphthalene]-2,5-dione, with the most promising functional profile, mixed 5-HT2A/D-2 antagonist and 5-HT1A partial agonist, was selected. In the mouse D-amphetamine-induced locomotor hyperactivity model, compound 14 produced antipsychotic-like activity, which is devoid of cataleptogenic effects and in the forced swim test in mice, it showed a significant antidepressant-like effect unlike the reference drug aripiprazole. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.04.026

文献信息

• Novel spirohydantoin derivative as a potent multireceptor-active antipsychotic and antidepressant agent
  作者：Anna Czopek、Marcin Kołaczkowski、Adam Bucki、Hanna Byrtus、Maciej Pawłowski、Grzegorz Kazek、Andrzej J. Bojarski、Agata Piaskowska、Justyna Kalinowska-Tłuścik、Anna Partyka、Anna Wesołowska

  DOI：10.1016/j.bmc.2015.04.026

  日期：2015.7

  A series of novel spirohydantoin derivatives with arylpiperazinylbutyl moiety were synthesized and evaluated for serotonin 5-HT1A, 5-HT2A, 5-HT7 and dopamine D-2 receptors. Based on these data, four compounds were selected for further binding affinity assays on dopamine D-1, D-3, D-4, and 5-HT2C, 5-HT6 as well as adrenergic alpha 1 and alpha(2C) receptors, which are involved in various CNS diseases such as schizophrenia, anxiety and/or depression. The compound 14, 1-4-[4-(2-metoxyphe-nyl) piperazin-1-yl] butyl}-3',4'-dihydro-2H, 2'H, 5H-spiro[imidazolidine-4,1'-naphthalene]-2,5-dione, with the most promising functional profile, mixed 5-HT2A/D-2 antagonist and 5-HT1A partial agonist, was selected. In the mouse D-amphetamine-induced locomotor hyperactivity model, compound 14 produced antipsychotic-like activity, which is devoid of cataleptogenic effects and in the forced swim test in mice, it showed a significant antidepressant-like effect unlike the reference drug aripiprazole. (C) 2015 Elsevier Ltd. All rights reserved.