3-{2-[Methyl-(2-pyrrolidin-1-yl-ethyl)-amino]-ethyl}-phenylamine

• 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: 3-{2-[Methyl-(2-pyrrolidin-1-yl-ethyl)-amino]-ethyl}-phenylamine
• 英文别名: 3-[2-[methyl(2-pyrrolidin-1-ylethyl)amino]ethyl]aniline
• 化学式: C₁₅H₂₅N₃
• mdl: MFCD21514272
• 分子量: 247.384
• InChiKey: MOLXMWFUMXCTFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  32.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-硝基苯乙酸 在 aluminium hydride 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 3-{2-[Methyl-(2-pyrrolidin-1-yl-ethyl)-amino]-ethyl}-phenylamine
  参考文献：
  名称：

  Synthesis and Evaluation of Aryl-Substituted N-(Arylethyl)-N-methyl-2-(1-pyrrolidinyl)ethylamines and Corresponding Arylacetamides for Sigma Receptor Affinity

  摘要：

  A series of aryl-monosubstituted arylacetamides (4-9) and arylethylenediamine (10-18) compounds were synthesized based on the structure of the high-affinity sigma ligand N-[2-(3 ,4-dichlorophenyl)ethyl] -N-nlethyl-2-(1-pyrrolidinyl)ethylamine (2). These compounds were prepared to evaluate the effect of aromatic substitution patterns on sigma-1 and sigma-2 receptor binding affinity and selectivity. The data indicate that 10-18 possessed higher affinity than 4-9 for both sigma sites, especially when substituted with an electron-withdrawing group. The diamine compounds 10-18 were selective for sigma-1 binding sites, whereas the arylacetamide compounds 4-9 generally exhibited an increased selectivity far sigma-2 sites compared to sigma-1. No clear pattern between the orientation of aromatic substituents and the sigma binding activity was observed.

  DOI：

  10.1021/jm9600813

文献信息

• Synthesis and Evaluation of Aryl-Substituted <i>N</i>-(Arylethyl)-<i>N</i>-methyl-2-(1-pyrrolidinyl)ethylamines and Corresponding Arylacetamides for Sigma Receptor Affinity
  作者：Ying Zhang、Wanda Williams、Wayne D. Bowen、Kenner C. Rice

  DOI：10.1021/jm9600813

  日期：1996.1.1

  A series of aryl-monosubstituted arylacetamides (4-9) and arylethylenediamine (10-18) compounds were synthesized based on the structure of the high-affinity sigma ligand N-[2-(3 ,4-dichlorophenyl)ethyl] -N-nlethyl-2-(1-pyrrolidinyl)ethylamine (2). These compounds were prepared to evaluate the effect of aromatic substitution patterns on sigma-1 and sigma-2 receptor binding affinity and selectivity. The data indicate that 10-18 possessed higher affinity than 4-9 for both sigma sites, especially when substituted with an electron-withdrawing group. The diamine compounds 10-18 were selective for sigma-1 binding sites, whereas the arylacetamide compounds 4-9 generally exhibited an increased selectivity far sigma-2 sites compared to sigma-1. No clear pattern between the orientation of aromatic substituents and the sigma binding activity was observed.