3-(5H-dibenzo[b,f]azepin-5-yl)propan-1-amine | 2064-34-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 3-(5H-dibenzo[b,f]azepin-5-yl)propan-1-amine
• 英文别名: 5-(3-Aminopropyl)-5H-dibenzazepin；Dibenz[b,f]azepine-5-propanamine；3-benzo[b][1]benzazepin-11-ylpropan-1-amine
• CAS: 2064-34-8
• 化学式: C₁₇H₁₈N₂
• 分子量: 250.343
• InChiKey: MUGJLOYKUDLEKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 3-(5H-dibenzo[b,f]azepin-5-yl)propan-1-amine 在 甲酸 作用下， 以 水 为溶剂， 反应 1.0h， 以64%的产率得到地帕明
  参考文献：
  名称：

  A Focused Library of Psychotropic Analogues with Neuroprotective and Neuroregenerative Potential

  摘要：

  Overcoming the lack of effective treatments and the continuous clinical trial failures in neurodegenerative drug discovery might require a shift from the prevailing paradigm targeting pathogenesis to the one targeting simultaneously neuroprotection and neuroregeneration. In the studies reported herein, we sought to identify small molecules that might exert neuroprotective and neuroregenerative potential as tools against neurodegenerative diseases. In doing so, we started from the reported neuroprotective/neuroregenerative mechanisms of psychotropic drugs featuring a tricyclic alkylamine scaffold. Thus, we designed a focused-chemical library of 36 entries aimed at exploring the structural requirements for efficient neuroprotective/neuroregenerative cellular activity, without the manifestation of toxicity. To this aim, we developed a synthetic protocol, which overcame the limited applicability of previously reported procedures. Next, we evaluated the synthesized compounds through a phenotypic screening pipeline, based on primary neuronal systems. Phenothiazine 2Bc showed improved neuroregenerative and neuroprotective properties with respect to reference drug desipramine (2Aa). Importantly, we have also shown that 2Bc outperformed currently available drugs in cell models of Alzheimer's and Parkinson's diseases and attenuates microglial activation by reducing iNOS expression.

  DOI：

  10.1021/acschemneuro.8b00242
• 作为产物：
  描述：

  N-(3-(5H-dibenzo[b,f]azepin-5-yl)propyl)acetamide 在 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 1.5h， 以79%的产率得到3-(5H-dibenzo[b,f]azepin-5-yl)propan-1-amine
  参考文献：
  名称：

  A Focused Library of Psychotropic Analogues with Neuroprotective and Neuroregenerative Potential

  摘要：

  Overcoming the lack of effective treatments and the continuous clinical trial failures in neurodegenerative drug discovery might require a shift from the prevailing paradigm targeting pathogenesis to the one targeting simultaneously neuroprotection and neuroregeneration. In the studies reported herein, we sought to identify small molecules that might exert neuroprotective and neuroregenerative potential as tools against neurodegenerative diseases. In doing so, we started from the reported neuroprotective/neuroregenerative mechanisms of psychotropic drugs featuring a tricyclic alkylamine scaffold. Thus, we designed a focused-chemical library of 36 entries aimed at exploring the structural requirements for efficient neuroprotective/neuroregenerative cellular activity, without the manifestation of toxicity. To this aim, we developed a synthetic protocol, which overcame the limited applicability of previously reported procedures. Next, we evaluated the synthesized compounds through a phenotypic screening pipeline, based on primary neuronal systems. Phenothiazine 2Bc showed improved neuroregenerative and neuroprotective properties with respect to reference drug desipramine (2Aa). Importantly, we have also shown that 2Bc outperformed currently available drugs in cell models of Alzheimer's and Parkinson's diseases and attenuates microglial activation by reducing iNOS expression.

  DOI：

  10.1021/acschemneuro.8b00242

文献信息

• [EN] METHODS AND COMPOSITIONS FOR TREATING MOOD DISORDER<br/>[FR] COMPOSITIONS ET METHODES DE TRAITEMENT DES TROUBLES DE L'HUMEUR
  申请人：WITTLIN WILLIAM A

  公开号：WO2005120523A1

  公开（公告）日：2005-12-22

  The invention relates to compositions and methods for treating mood spectrum disorder. The compositions relate to novel combinations and formulations of pharmaceutical compounds for treatment of mood spectrum disorders. The methods provide for use of the compounds provided herein for the treatment of mood spectrum disorders in addition to the use of mood screens for diagnosing a patient.

  本发明涉及用于治疗情绪谱系障碍的组合物和方法。所述组合物涉及用于治疗情绪谱系障碍的新型药物化合物的组合和制剂。所述方法提供了使用本文提供的化合物治疗情绪谱系障碍的方法，以及使用情绪筛查诊断患者的方法。
• METHODS AND COMPOSITIONS FOR TREATING MOOD DISORDER
  申请人：Mood Management Sciences, LLC

  公开号：EP1758600A1

  公开（公告）日：2007-03-07
• EP1758600A4
  申请人：——

  公开号：EP1758600A4

  公开（公告）日：2008-03-05
• Methods and Compositions for Treating Mood Disorder
  申请人：Wittlin A. William

  公开号：US20070264358A1

  公开（公告）日：2007-11-15

  The invention relates to compositions and methods for treating mood spectrum disorder. The compositions relate to novel combinations and formulations of pharmaceutical compounds for treatment of mood spectrum disorders. The methods provide for use of the compounds provided herein for the treatment of mood spectrum disorders in addition to the use of mood screens for diagnosing a patient.
• US7790905B2
  申请人：——

  公开号：US7790905B2

  公开（公告）日：2010-09-07