N-(3-(benzyloxy)-2-methoxybenzyl)-2-(4-(benzyloxy)-3-methoxyphenyl)ethan-1-amine

• 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-(3-(benzyloxy)-2-methoxybenzyl)-2-(4-(benzyloxy)-3-methoxyphenyl)ethan-1-amine
• 英文别名: 2-(3-methoxy-4-phenylmethoxyphenyl)-N-[(2-methoxy-3-phenylmethoxyphenyl)methyl]ethanamine
• 化学式: C₃₁H₃₃NO₄
• 分子量: 483.607
• InChiKey: IZBICEOCAVGDOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  49
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙缩醛 、 N-(3-(benzyloxy)-2-methoxybenzyl)-2-(4-(benzyloxy)-3-methoxyphenyl)ethan-1-amine 在 三氟乙酸 、 盐酸 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 3.0h， 以60%的产率得到2-(3-hydroxy-2-methoxybenzyl)-6-methoxy-1-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol
  参考文献：
  名称：

  Tetrahydroprotoberberine alkaloids with dopamine and σ receptor affinity

  摘要：

  Two series of analogues of the tetrahydroprotoberberine (THPB) alkaloid (+/-)-stepholidine that (a) contain various alkoxy substituents at the C10 position and, (b) were de-rigidified with respect to (+/-)-stepholidine, were synthesized and evaluated for affinity at dopamine and sigma receptors in order to evaluate effects on D3 and sigma 2 receptor affinity and selectivity. Small n-alkoxy groups are best tolerated by D3 and sigma 2 receptors. Among all compounds tested, C10 methoxy and ethoxy analogues (10 and 11 respectively) displayed the highest affinity for sigma 2 receptors as well as sigma 2 versus sigma 1 selectivity and also showed the highest D3 receptor affinity. De-rigidification of stepholidine resulted in decreased affinity at all receptors evaluated; thus the tetracyclic THPB framework is advantageous for affinity at dopamine and sigma receptors. Docking of the C10 analogues at the D3 receptor, suggest that an ionic interaction between the protonated nitrogen atom and Asp110, a H-bond interaction between the C2 phenol and Ser192, a H-bond interaction between the C10 phenol and Cys181 as well as hydrophobic interactions of the aryl rings to Phe106 and Phe345, are critical for high affinity of the compounds. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.03.037
• 作为产物：
  描述：

  4-苄氧基-3-甲氧基苯乙胺 、 3-benzyloxy-2-methoxybenzaldehyde 在 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 为溶剂， 反应 3.17h， 以83%的产率得到N-(3-(benzyloxy)-2-methoxybenzyl)-2-(4-(benzyloxy)-3-methoxyphenyl)ethan-1-amine
  参考文献：
  名称：

  Tetrahydroprotoberberine alkaloids with dopamine and σ receptor affinity

  摘要：

  Two series of analogues of the tetrahydroprotoberberine (THPB) alkaloid (+/-)-stepholidine that (a) contain various alkoxy substituents at the C10 position and, (b) were de-rigidified with respect to (+/-)-stepholidine, were synthesized and evaluated for affinity at dopamine and sigma receptors in order to evaluate effects on D3 and sigma 2 receptor affinity and selectivity. Small n-alkoxy groups are best tolerated by D3 and sigma 2 receptors. Among all compounds tested, C10 methoxy and ethoxy analogues (10 and 11 respectively) displayed the highest affinity for sigma 2 receptors as well as sigma 2 versus sigma 1 selectivity and also showed the highest D3 receptor affinity. De-rigidification of stepholidine resulted in decreased affinity at all receptors evaluated; thus the tetracyclic THPB framework is advantageous for affinity at dopamine and sigma receptors. Docking of the C10 analogues at the D3 receptor, suggest that an ionic interaction between the protonated nitrogen atom and Asp110, a H-bond interaction between the C2 phenol and Ser192, a H-bond interaction between the C10 phenol and Cys181 as well as hydrophobic interactions of the aryl rings to Phe106 and Phe345, are critical for high affinity of the compounds. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.03.037