2-[(3S)-3-(3,4-dichlorophenyl)-1,2,4,7-tetrahydroazepin-3-yl]ethanol | 1413938-82-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[(3S)-3-(3,4-dichlorophenyl)-1,2,4,7-tetrahydroazepin-3-yl]ethanol
• CAS: 1413938-82-5
• 化学式: C₁₄H₁₇Cl₂NO
• 分子量: 286.201
• InChiKey: WJWXUKMOYJEIRB-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3,4-二氯苯乙腈 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 盐酸 、 甲醇 、 水 、 四丁基碘化铵 、 三乙酰氧基硼氢化钠 、 sodium hydride 、 二异丁基氢化铝 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 、 甲苯 、 乙腈 为溶剂， 反应 104.0h， 生成 2-[(3S)-3-(3,4-dichlorophenyl)-1,2,4,7-tetrahydroazepin-3-yl]ethanol 、 2-[(3R)-3-(3,4-dichlorophenyl)-1,2,4,7-tetrahydroazepin-3-yl]ethanol
  参考文献：
  名称：

  Azepines and Piperidines with Dual Norepinephrine Dopamine Uptake Inhibition and Antidepressant Activity

  摘要：

  Herein, we describe the discovery of inhibitors of norepinephrine (NET) and dopamine (DAT) transporters with reduced activity relative to serotonin transporters (SERT). Two compounds, 8b and 21a, along with nomifensine were tested in a rodent receptor occupancy study and demonstrated dose-dependent displacement of radiolabeled NET and DAT ligands. These compounds were efficacious in a rat forced swim assay (model of depression) and also had activity in rat spontaneous locomotion assay.

  DOI：

  10.1021/ml300262e

文献信息

• Azepines and Piperidines with Dual Norepinephrine Dopamine Uptake Inhibition and Antidepressant Activity
  作者：Dean G. Brown、Peter R. Bernstein、Ye Wu、Rebecca A. Urbanek、Christopher W. Becker、Scott R. Throner、Bruce T. Dembofsky、Gary B. Steelman、Lois A. Lazor、Clay W. Scott、Michael W. Wood、Steven S. Wesolowski、David A. Nugiel、Stephanie Koch、Jian Yu、Donald E. Pivonka、Shuang Li、Carol Thompson、Anna Zacco、Charles S. Elmore、Patricia Schroeder、JianWei Liu、Christopher A. Hurley、Stuart Ward、Hazel J. Hunt、Karen Williams、Joseph McLaughlin、Valerie Hoesch、Simon Sydserff、Donna Maier、David Aharony

  DOI：10.1021/ml300262e

  日期：2013.1.10

  Herein, we describe the discovery of inhibitors of norepinephrine (NET) and dopamine (DAT) transporters with reduced activity relative to serotonin transporters (SERT). Two compounds, 8b and 21a, along with nomifensine were tested in a rodent receptor occupancy study and demonstrated dose-dependent displacement of radiolabeled NET and DAT ligands. These compounds were efficacious in a rat forced swim assay (model of depression) and also had activity in rat spontaneous locomotion assay.