(S)-4-((3,5-bis(trifluoromethyl)benzyloxy)methyl)-4-phenylazepane | 874454-07-6

• 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: (S)-4-((3,5-bis(trifluoromethyl)benzyloxy)methyl)-4-phenylazepane
• 英文别名: (4S)-4-[[3,5-bis(trifluoromethyl)phenyl]methoxymethyl]-4-phenylazepane
• CAS: 874454-07-6
• 化学式: C₂₂H₂₃F₆NO
• 分子量: 431.421
• InChiKey: QLXHEEVESGWCHN-HXUWFJFHSA-N

物化性质

• 沸点：
  408.6±45.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-4-((3,5-bis(trifluoromethyl)benzyloxy)methyl)-4-phenylazepane 、 苯甲醛 在 sodium cyanoborohydride 、 三氟乙酸 作用下， 以 甲醇 、 四氢呋喃 为溶剂， 反应 0.5h， 生成 (S)-4-((3,5-bis(trifluoromethyl)benzyloxy)methyl)-1-benzyl-4-phenylazepane
  参考文献：
  名称：

  Discovery of disubstituted piperidines and homopiperidines as potent dual NK 1 receptor antagonists–serotonin reuptake transporter inhibitors for the treatment of depression

  摘要：

  This report describes the synthesis, structure-activity relationships and activity of piperidine, homopiperidine, and azocane derivatives combining NK1 receptor (NK1R) antagonism and serotonin reuptake transporter (SERT) inhibition. Our studies culminated in the discovery of piperidine 2 and homopiperidine 8 as potent dual NK1R antagonists-SERT inhibitors. Compound 2 demonstrated significant activity in the gerbil forced swimming test, suggesting that dual NK1R antagonists-SERT inhibitors may be useful in treating depression disorders. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.02.010
• 作为产物：
  描述：

  1-(((3,3-ethylenedioxy-1-phenylcyclohexyl)methoxy)methyl)-3,5-bis(trifluoromethyl)benzene 在 盐酸 、 sodium azide 、 硼烷四氢呋喃络合物 、 三氟乙酸 作用下， 以 水 、 丙酮 、 苯 为溶剂， 反应 5.0h， 生成 (S)-4-((3,5-bis(trifluoromethyl)benzyloxy)methyl)-4-phenylazepane
  参考文献：
  名称：

  Discovery of disubstituted piperidines and homopiperidines as potent dual NK 1 receptor antagonists–serotonin reuptake transporter inhibitors for the treatment of depression

  摘要：

  This report describes the synthesis, structure-activity relationships and activity of piperidine, homopiperidine, and azocane derivatives combining NK1 receptor (NK1R) antagonism and serotonin reuptake transporter (SERT) inhibition. Our studies culminated in the discovery of piperidine 2 and homopiperidine 8 as potent dual NK1R antagonists-SERT inhibitors. Compound 2 demonstrated significant activity in the gerbil forced swimming test, suggesting that dual NK1R antagonists-SERT inhibitors may be useful in treating depression disorders. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.02.010

文献信息

• Homopiperidine derivatives as NK-1 antagonists
  申请人：Wu Yong-Jin

  公开号：US20060019943A1

  公开（公告）日：2006-01-26

  The present disclosure relates to chemical compounds and their use in human therapy. In a specific embodiment, compounds of Formula (I) or an isomer, a pharmaceutically acceptable salt or solvate thereof or a pharmaceutically acceptable formulation comprising said compounds useful for the treatment or prevention of conditions mediated by tachykinins and/or selective inhibition of serotonin reuptake transporter protein. The compounds act as dual NK-1 antagonists and selective serotonin reuptake inhibitors.

  本公开涉及化合物及其在人类治疗中的应用。在一个具体实施例中，公式（I）的化合物或其异构体，药学上可接受的盐或溶剂，或包含该化合物的药学上可接受的制剂，用于治疗或预防由缓激肽介导的疾病和/或选择性抑制血清素再摄取转运蛋白的条件。这些化合物作为双重NK-1拮抗剂和选择性血清素再摄取抑制剂。
• Discovery of disubstituted piperidines and homopiperidines as potent dual NK 1 receptor antagonists–serotonin reuptake transporter inhibitors for the treatment of depression
  作者：Yong-Jin Wu、Huan He、Robert Bertekap、Ryan Westphal、Snjezana Lelas、Amy Newton、Tanya Wallace、Matthew Taber、Carl Davis、John E. Macor、Joanne Bronson

  DOI：10.1016/j.bmc.2013.02.010

  日期：2013.4

  This report describes the synthesis, structure-activity relationships and activity of piperidine, homopiperidine, and azocane derivatives combining NK1 receptor (NK1R) antagonism and serotonin reuptake transporter (SERT) inhibition. Our studies culminated in the discovery of piperidine 2 and homopiperidine 8 as potent dual NK1R antagonists-SERT inhibitors. Compound 2 demonstrated significant activity in the gerbil forced swimming test, suggesting that dual NK1R antagonists-SERT inhibitors may be useful in treating depression disorders. (C) 2013 Elsevier Ltd. All rights reserved.