2-[2-Methoxy-5-(3-phenyl-propyl)-phenyl]-1-methyl-ethylamine

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2-[2-Methoxy-5-(3-phenyl-propyl)-phenyl]-1-methyl-ethylamine
• 英文别名: 1-[2-methoxy-5-(3-phenylpropyl)phenyl]propan-2-amine
• 化学式: C₁₉H₂₅NO
• 分子量: 283.414
• InChiKey: QVJYLZMOZOXXCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-苯丙酰氯 在 10percent Pd/C 氢气 、 四氯化钛 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、310.27 kPa 条件下， 反应 79.5h， 生成 2-[2-Methoxy-5-(3-phenyl-propyl)-phenyl]-1-methyl-ethylamine
  参考文献：
  名称：

  1-[2-Methoxy-5-(3-phenylpropyl)]-2-aminopropane Unexpectedly Shows 5-HT_2A Serotonin Receptor Affinity and Antagonist Character

  摘要：

  Certain phenylethylamines, such as 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane (DOB; 1a), are high-affinity 5-HT2 agonists. Previous structure-affinity studies have concluded that both the 2,5-dimethoxy substitution pattern and the nature of substituents at the 4-position are important determinants of high affinity. We recently demonstrated that replacement of the bromo group of DOB with a 3-(phenyl)propyl substituent results in retention of affinity and that, counter to established structure-affinity relationships, the 2,5-dimethoxy substitution pattern is no longer a requirement for the binding. The present investigation extends these findings by examining a series of analogues, 3, lacking a 5-methoxy group. It was additionally found that shifting the phenylalkyl substituent from the 4- to the 5-position (e.g., 4i) also results in retention of affinity. For example, 1-(2-methoxy-5-(3-phenylpropyl)-2-aminopropane (6; the alpha -methyl derivative of 4i) binds at 5-HT2A receptors with high affinity (K-i = 13 nM) and possesses 5-HT2A antagonist character. Thus, not only is the 2,5-dimethoxy substitution pattern not a requirement for the binding of certain phenylethylamines at 5-HT2A receptors, the presence of a 4-position substituent (previously thought to serve as a modulator of affinity of DOB-like agents) is also not required. Striking differences in the 5-HT2A binding requirements of the present compounds as compared to DOB-like agents suggest multiple substituent-dependent modes of binding.

  DOI：

  10.1021/jm0100739