N-hexyl-2-(3-methoxyphenyl)-N-phenethylethaneamine | 1409931-98-1

• 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: N-hexyl-2-(3-methoxyphenyl)-N-phenethylethaneamine
• 英文别名: N-[2-(3-methoxyphenyl)ethyl]-N-(2-phenylethyl)hexan-1-amine
• CAS: 1409931-98-1
• 化学式: C₂₃H₃₃NO
• 分子量: 339.521
• InChiKey: QZFXKQIEDXTSSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-hexyl-2-(3-methoxyphenyl)-N-phenethylethaneamine 在 乙硫醇钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 3-[2-[Hexyl(Phenethyl)Amino]Ethyl]Phenol
  参考文献：
  名称：

  Discovery and Pharmacological Evaluation of a Diphenethylamine Derivative (HS665), a Highly Potent and Selective κ Opioid Receptor Agonist

  摘要：

  Here we report on the design, synthesis, and biological characterization of novel kappa opioid (KOP) receptor ligands of diphenethylamines. In opioid receptor binding and functional assays, the N-cyclobutylmethyl substituted derivative 4 (HS665) showed the highest affinity and selectivity for the KOP receptor and KOP-agonist potency. Compound 4 inhibited acetic acid induced writhing after subcutaneous administration in mice via KOP receptor mediated mechanisms, being equipotent as an analgesic to the KOP agonist U50,488.

  DOI：

  10.1021/jm301258w
• 作为产物：
  描述：

  3-甲氧基苯乙胺 在 sodium cyanoborohydride 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 100.5h， 生成 N-hexyl-2-(3-methoxyphenyl)-N-phenethylethaneamine
  参考文献：
  名称：

  Discovery and Pharmacological Evaluation of a Diphenethylamine Derivative (HS665), a Highly Potent and Selective κ Opioid Receptor Agonist

  摘要：

  Here we report on the design, synthesis, and biological characterization of novel kappa opioid (KOP) receptor ligands of diphenethylamines. In opioid receptor binding and functional assays, the N-cyclobutylmethyl substituted derivative 4 (HS665) showed the highest affinity and selectivity for the KOP receptor and KOP-agonist potency. Compound 4 inhibited acetic acid induced writhing after subcutaneous administration in mice via KOP receptor mediated mechanisms, being equipotent as an analgesic to the KOP agonist U50,488.

  DOI：

  10.1021/jm301258w

文献信息

• Discovery and Pharmacological Evaluation of a Diphenethylamine Derivative (HS665), a Highly Potent and Selective κ Opioid Receptor Agonist
  作者：Mariana Spetea、Ilona P. Berzetei-Gurske、Elena Guerrieri、Helmut Schmidhammer

  DOI：10.1021/jm301258w

  日期：2012.11.26

  Here we report on the design, synthesis, and biological characterization of novel kappa opioid (KOP) receptor ligands of diphenethylamines. In opioid receptor binding and functional assays, the N-cyclobutylmethyl substituted derivative 4 (HS665) showed the highest affinity and selectivity for the KOP receptor and KOP-agonist potency. Compound 4 inhibited acetic acid induced writhing after subcutaneous administration in mice via KOP receptor mediated mechanisms, being equipotent as an analgesic to the KOP agonist U50,488.