N,N-dimethyl-3-(2-methoxyphenoxy)propanamine | 75384-45-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N,N-dimethyl-3-(2-methoxyphenoxy)propanamine
• 英文别名: 3-(2-methoxyphenoxy)-N,N-dimethylpropan-1-amine
• CAS: 75384-45-1
• 化学式: C₁₂H₁₉NO₂
• mdl: MFCD06304708
• 分子量: 209.288
• InChiKey: LPXILBCDKVWPAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(3-溴丙氧基)-2-甲氧基苯 、 盐酸二甲胺 在 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 N,N-dimethyl-3-(2-methoxyphenoxy)propanamine
  参考文献：
  名称：

  Design and synthesis of propranolol analogs as serotonergic agents

  摘要：

  Serotonin (5-HT) binds with nearly identical affinity at the various central 5-HT binding sites. Few agents bind with selectivity for 5-HT1A sites. The beta-adrenergic antagonist propranolol binds stereoselectively both at 5-HT1A and 5-HT1B sites (with a several-fold selectivity for the latter) and, whereas it is a 5-HT1A antagonist, it appears to be a 5-HT1B agonist. As such, it could serve as a lead compound for the development of new 5-HT1A and 5-HT1B agents. The purpose of the present study was to modify the structure of propranolol in such a manner so as to reduce its affinity for 5-HT1B and beta-adrenergic sites while, at the same time, retaining its affinity for 5-HT1A sites. Removal of the side-chain hydroxyl group of propranolol, and conversion of its secondary amine to a tertiary amine, reduced affinity for 5-HT1B and beta-adrenergic sites. In addition, shortening the side chain by one carbon atom resulted in compounds with affinity for hippocampal 5-HT1A sites comparable to that of racemic propranolol, but with a 30- to 500-fold lower affinity for 5-HT1B sites and a greater than 1000-fold lower affinity for beta-adrenergic sites. The results of these preliminary studies attest to the utility of this approach for the development of novel serotonergic agents.

  DOI：

  10.1021/jm00124a021