1-(3-(naphthalen-1-yl)propyl)piperazine | 1266207-45-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(3-(naphthalen-1-yl)propyl)piperazine
• 英文别名: 1-(3-Naphthalen-1-ylpropyl)piperazine
• CAS: 1266207-45-7
• 化学式: C₁₇H₂₂N₂
• 分子量: 254.375
• InChiKey: QLKRKRKECOFMII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(3-(naphthalen-1-yl)propyl)piperazine 、 N-Boc-2,6-二甲基-L-酪氨酸 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 6-氯-1-羟基苯并三氮唑 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (S)-2-amino-3-(4-hydroxy-2,6-dimethylphenyl)-1-(4-(3-(naphthalen-1-yl)propyl)piperazin-1-yl)propan-1-one
  参考文献：
  名称：

  Synthesis and evaluation of 4-substituted piperidines and piperazines as balanced affinity μ opioid receptor (MOR) agonist/δ opioid receptor (DOR) antagonist ligands

  摘要：

  In this letter, we describe a series of 4-substituted piperidine and piperazine compounds based on tetrahydroquinoline 1, a compound that shows balanced, low nanomolar binding affinity for the mu opioid receptor (MOR) and the delta opioid receptor (DOR). We have shown that by changing the length and flexibility profile of the side chain in this position, binding affinity is improved at both receptors by a significant degree. Furthermore, several of the compounds described herein display good efficacy at MOR, while simultaneously displaying DOR antagonism. The MOR agonist/DOR antagonist has shown promise in the reduction of negative side effects displayed by selective MOR agonists, namely the development of dependence and tolerance. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.021
• 作为产物：
  描述：

  3-(萘-1-基)丙酸甲酯 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 1-(3-(naphthalen-1-yl)propyl)piperazine
  参考文献：
  名称：

  Synthesis and evaluation of 4-substituted piperidines and piperazines as balanced affinity μ opioid receptor (MOR) agonist/δ opioid receptor (DOR) antagonist ligands

  摘要：

  In this letter, we describe a series of 4-substituted piperidine and piperazine compounds based on tetrahydroquinoline 1, a compound that shows balanced, low nanomolar binding affinity for the mu opioid receptor (MOR) and the delta opioid receptor (DOR). We have shown that by changing the length and flexibility profile of the side chain in this position, binding affinity is improved at both receptors by a significant degree. Furthermore, several of the compounds described herein display good efficacy at MOR, while simultaneously displaying DOR antagonism. The MOR agonist/DOR antagonist has shown promise in the reduction of negative side effects displayed by selective MOR agonists, namely the development of dependence and tolerance. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.021

文献信息

• SIGMA RECEPTOR LIGANDS AND THE USE THEREOF
  申请人：VIRGINIA COMMONWEALTH UNIVERSITY

  公开号：EP0507863A1

  公开（公告）日：1992-10-14
• EP0507863A4
  申请人：——

  公开号：EP0507863A4

  公开（公告）日：1993-07-07
• [EN] SIGMA RECEPTOR LIGANDS AND THE USE THEREOF
  申请人：——

  公开号：WO1991009594A1

  公开（公告）日：1991-07-11

  [EN] The invention relates to methods for the treatment of schizophrenia or other psychoses by administering a pharmaceutical composition comprising an effective amount of certain sigma receptor ligands to a patient in need of such treatment. The invention further relates to novel sigma receptor ligands having high binding to the sigma receptor and pharmaceutical compositions thereof.
  [FR] Procédés de traitement de la schizophrénie ou d'autres psychoses, par administration d'une composition pharmaceutique comprenant une quantité efficace de certains ligands de récepteur sigma, à un patient nécessitant un tel traitement. L'invention concerne également de nouveaux ligands de récepteur sigma, présentant une liaison élevée aux récepteurs sigma, ainsi que leurs compositions pharmaceutiques.