1-[2,5-dimethoxy-4-(3-phenylpropyl)phenyl]-2-aminopropane | 125903-72-2

• 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: 1-[2,5-dimethoxy-4-(3-phenylpropyl)phenyl]-2-aminopropane
• 英文别名: 1-(2,5-Dimethoxy-4-(3-phenylpropyl)phenyl)propan-2-amine；1-[2,5-dimethoxy-4-(3-phenylpropyl)phenyl]propan-2-amine
• CAS: 125903-72-2
• 化学式: C₂₀H₂₇NO₂
• 分子量: 313.44
• InChiKey: XKCYCNKOOGOHIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-苯丙酰氯 在 palladium on activated charcoal sodium hydroxide 、 高氯酸 、 氢气 、 四氯化钛 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 9.0h， 生成 1-[2,5-dimethoxy-4-(3-phenylpropyl)phenyl]-2-aminopropane
  参考文献：
  名称：

  A structure-affinity study of the binding of 4-substituted analogs of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors

  摘要：

  With [3H]ketanserin as the radioligand, structure-affinity relationships (SAFIRs) for binding at central 5-HT2 serotonin receptors (rat frontal cortex) were examined for a series of 27 4-substituted 1-(2,5-dimethoxyphenyl)-2-aminopropane derivatives (2,5-DMAs). The affinity (Ki values) ranged over a span of several orders of magnitude. It appears that the lipophilic character of the 4-position substituent plays a major role in determining the affinity of these agents for 5-HT2 receptors, 2,5-DMAs with polar 4-substituents (e.g. OH, NH2, COOH) display a very low affinity (Ki greater than 25,000 nM) for these receptors, whereas those with lipophilic functions display a significantly higher affinity. The results of these studies prompted us to synthesize and evaluate examples of newer lipophilic derivatives and several of these (e.g. n-hexyl, n-octyl) bind with very high (Ki values = 2.5 and 3 nM, respectively) affinities at central 5-HT2 sites. Although, 2,5-DMAs are generally considered to be 5-HT2 agonists, preliminary studies with isolated rat thoracic aorta suggest that some of the more lipophilic derivatives (e.g. the n-hexyl and n-octyl derivatives) are 5-HT2 antagonists.

  DOI：

  10.1021/jm00165a023