2-[2-(Naphthalen-1-yloxy)-ethylamino]-ethanol | 199453-88-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-[2-(Naphthalen-1-yloxy)-ethylamino]-ethanol
• 英文别名: 2-(2-naphthalen-1-yloxyethylamino)ethanol
• CAS: 199453-88-8
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: JRPNGLICMSJWSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(1-萘氧基)乙醇 在 吡啶 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 51.0h， 生成 2-[2-(Naphthalen-1-yloxy)-ethylamino]-ethanol
  参考文献：
  名称：

  2-(1-Naphthyloxy)ethylamines with Enhanced Affinity for Human 5-HT_1Dβ (h5-HT_1B) Serotonin Receptors

  摘要：

  Although the beta-adrenergic antagonist propranolol (1) binds at rodent 5-HT1B serotonin receptors, it displays low affinity (K-i > 10 000 nM) for its species homologue 5-HT1D beta (i.e., h5-HT1B) receptors. The structure of propranolol was systematically modified in an attempt to enhance its affinity for the latter population of receptors. Removal of the alkyl hydroxyl group, shortening of the O-alkyl chain from three to two methylene groups, and variation of the terminal amine substituent resulted in compounds, such as N-monomethyl-2-(1-naphthyloxy)ethylamine (11; K-i = 26 nM), that display significantly higher h5-HT1B affinity than propranolol. Compound 11 was shown to bind equally well at human 5-HT1D alpha (h5-HT1D) receptors (K-i = 34 nM) and was further demonstrated to possess h5-HT1B agonist character in an adenylate cyclase assay. It would appear that such (aryloxy)alkylamines may represent a novel class of 5-HT1D receptor agonists.

  DOI：

  10.1021/jm970507t