N-n-propyl-N-<2-(2-methoxy-4-pyridyl)ethyl>-2-phenylethanamide | 170026-06-9

• 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-n-propyl-N-<2-(2-methoxy-4-pyridyl)ethyl>-2-phenylethanamide
• 英文别名: N-[2-(2-methoxypyridin-4-yl)ethyl]-2-phenyl-N-propylacetamide
• CAS: 170026-06-9
• 化学式: C₁₉H₂₄N₂O₂
• 分子量: 312.412
• InChiKey: JARIBRFOYVYPLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-n-propyl-N-<2-(2-methoxy-4-pyridyl)ethyl>-2-phenylethanamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 32.0h， 以91%的产率得到N-propyl-N-(2-phenylethyl)-2-(2-methoxy-4-pyridyl)ethylamine
  参考文献：
  名称：

  New 2-pyridylethylamines with dopaminergic activity: Synthesis and radioligand-binding evaluation

  摘要：

  In order to determine whether the pyridine nucleus could replace the catechol moiety of the neurotransmitter dopamine or the phenol ring of the dopaminergic pharmacophore m-hydroxyphenylethylamine, the 2-(3-pyridyl)ethylamine 7, 2-(4-pyridyl)ethylamine 8, 2-(2-hydroxy-4-pyridyl) ethylamine 10 and their N,N-di-n-propyl- and N-n-propyl-N-2-phenylethyl derivatives were synthesized. The affinities of the new compounds for D-1 and D-2 dopamine receptors were evaluated by displacement of [H-3]SCH 23390 (D-1 selective) and [H-3]spiperone (D-2 selective) on rat neostriatum sections. The 2-(4-pyridyl)ethylamine 8 and its N,N-di-n-propyl derivative 18 showed the same affinity for the D-1 and D-2 receptors. Other compounds bound to the D-1 receptor with higher affinity than to the D-2 receptor. The possibility that the above compounds act as agonists and antagonists at the dopamine D-1 and D-2 receptors is discussed on the basis of guanosine-5'-triphosphate and Na+ displacement curves.

  DOI：

  10.1016/0223-5234(96)88251-1
• 作为产物：
  描述：

  2-甲氧基-4-吡啶丙酸 在 sodium tetrahydroborate 、 sodium azide 、 硫酸 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 54.0h， 生成 N-n-propyl-N-<2-(2-methoxy-4-pyridyl)ethyl>-2-phenylethanamide
  参考文献：
  名称：

  New 2-pyridylethylamines with dopaminergic activity: Synthesis and radioligand-binding evaluation

  摘要：

  In order to determine whether the pyridine nucleus could replace the catechol moiety of the neurotransmitter dopamine or the phenol ring of the dopaminergic pharmacophore m-hydroxyphenylethylamine, the 2-(3-pyridyl)ethylamine 7, 2-(4-pyridyl)ethylamine 8, 2-(2-hydroxy-4-pyridyl) ethylamine 10 and their N,N-di-n-propyl- and N-n-propyl-N-2-phenylethyl derivatives were synthesized. The affinities of the new compounds for D-1 and D-2 dopamine receptors were evaluated by displacement of [H-3]SCH 23390 (D-1 selective) and [H-3]spiperone (D-2 selective) on rat neostriatum sections. The 2-(4-pyridyl)ethylamine 8 and its N,N-di-n-propyl derivative 18 showed the same affinity for the D-1 and D-2 receptors. Other compounds bound to the D-1 receptor with higher affinity than to the D-2 receptor. The possibility that the above compounds act as agonists and antagonists at the dopamine D-1 and D-2 receptors is discussed on the basis of guanosine-5'-triphosphate and Na+ displacement curves.

  DOI：

  10.1016/0223-5234(96)88251-1

文献信息

• New 2-pyridylethylamines with dopaminergic activity: Synthesis and radioligand-binding evaluation
  作者：F Claudi、GM Cingolani、G Giorgioni、M Cardellini、F Amenta、C Polidori

  DOI：10.1016/0223-5234(96)88251-1

  日期：1995.1

  In order to determine whether the pyridine nucleus could replace the catechol moiety of the neurotransmitter dopamine or the phenol ring of the dopaminergic pharmacophore m-hydroxyphenylethylamine, the 2-(3-pyridyl)ethylamine 7, 2-(4-pyridyl)ethylamine 8, 2-(2-hydroxy-4-pyridyl) ethylamine 10 and their N,N-di-n-propyl- and N-n-propyl-N-2-phenylethyl derivatives were synthesized. The affinities of the new compounds for D-1 and D-2 dopamine receptors were evaluated by displacement of [H-3]SCH 23390 (D-1 selective) and [H-3]spiperone (D-2 selective) on rat neostriatum sections. The 2-(4-pyridyl)ethylamine 8 and its N,N-di-n-propyl derivative 18 showed the same affinity for the D-1 and D-2 receptors. Other compounds bound to the D-1 receptor with higher affinity than to the D-2 receptor. The possibility that the above compounds act as agonists and antagonists at the dopamine D-1 and D-2 receptors is discussed on the basis of guanosine-5'-triphosphate and Na+ displacement curves.