Isopropyl-[2-(naphthalen-1-yloxy)-ethyl]-amine | 85262-35-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Isopropyl-[2-(naphthalen-1-yloxy)-ethyl]-amine
• 英文别名: N-(2-naphthalen-1-yloxyethyl)propan-2-amine
• CAS: 85262-35-7
• 化学式: C₁₅H₁₉NO
• mdl: MFCD11200250
• 分子量: 229.322
• InChiKey: IKOVVHZXLBYZJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

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 Isopropyl-[2-(naphthalen-1-yloxy)-ethyl]-amine
  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

文献信息

• Nickel‐Catalyzed Chemoselective Arylation of Amino Alcohols
  作者：Kathleen Morrison、Charles Yeung、Mark Stradiotto

  DOI：10.1002/anie.202300686

  日期：——

  An evaluation of competitive bisphosphine/Ni-catalyzed C−N versus C−O cross-couplings involving model compounds enabled development of chemoselective, metal-catalyzed O- and N-arylation of amino alcohols with (hetero)aryl chloride electrophiles, without recourse to protection group chemistry.

  对涉及模型化合物的竞争性双膦/Ni 催化的 C−N 与 C−O 交叉偶联的评估使得能够开发化学选择性、金属催化的 O - 和 N -氨基醇与（杂）芳基氯亲电子试剂的芳基化，而无需求助于保护基化学。
• N-(aryloxyalkyl)-N'-(amino-alkyl) ureas
  申请人：A.H. ROBINS COMPANY, INCORPORATED

  公开号：EP0066987B1

  公开（公告）日：1986-08-27
• US4500529A
  申请人：——

  公开号：US4500529A

  公开（公告）日：1985-02-19
• US4558155A
  申请人：——

  公开号：US4558155A

  公开（公告）日：1985-12-10
• 2-(1-Naphthyloxy)ethylamines with Enhanced Affinity for Human 5-HT_1D_β (h5-HT_1B) Serotonin Receptors
  作者：Abd M. Ismaiel、Malgorzata Dukat、Ho Law、Rajender Kamboj、Ermi Fan、David K. H. Lee、Lucia Mazzocco、Donna Buekschkens、Milt Teitler、Myles E. Pierson、Richard A. Glennon

  DOI：10.1021/jm970507t

  日期：1997.12.1

  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.