N-methyl-4-(4-methoxyphenyl)butylamine | 89745-31-3

• 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-methyl-4-(4-methoxyphenyl)butylamine
• 英文别名: Benzenebutanamine, 4-methoxy-N-methyl-；4-(4-methoxyphenyl)-N-methylbutan-1-amine
• CAS: 89745-31-3
• 化学式: C₁₂H₁₉NO
• 分子量: 193.289
• InChiKey: IRYPMKXHLFMIBU-UHFFFAOYSA-N

物化性质

• 沸点：
  298.3±23.0 °C(Predicted)
• 密度：
  0.944±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 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：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-methyl-4-(4-methoxyphenyl)butylamine 在 盐酸 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 5.0h， 生成 6-fluoro-8-{2-[N-methyl-4-(4-methoxyphenyl)butylamino]ethoxy}chroman-4-one
  参考文献：
  名称：

  Synthesis and Pharmacological Characterization of Novel 6-Fluorochroman Derivatives as Potential 5-HT_1A Receptor Antagonists

  摘要：

  A series of novel 6-fluorochroman derivatives was prepared and evaluated as antagonists for the 5-HT1A receptor. N-2- [[(6-Fluorochroman-8-yl)oxy]ethyl]-4-(4-methoxyphenyl)butylamine (3; J. Med. Chem. 1997, 40, 1252-1257) was chosen as a lead, and structural modifications were done on the aliphatic portion of the chroman ring, the tether linking the middle amine and the terminal aromatic ring, the aromatic ring, and lastly the amine. Radioligand binding assays proved that the majority of the novel compounds behaved as good to excellent ligands at the 5-HT1A receptor, some of which were selective with respect to alpha(1)-adrenergic and D-2-dopaminergic receptors. The antagonist activity of the compounds was assessed in the forskolin-stimulated adenylate cyclase assays in CHO cells expressing the human 5-HT1A receptors. Among the modifications attempted, introduction of an oxo or an optically active hydroxy moiety at the chroman C-4 position was effective in ameliorating the receptor selectivity. Six analogues were selected through the in vitro screeds and further evaluated for their in vivo activities. A 4-oxochroman derivative (31n), having a terminal 1,3-benzodioxole ring, demonstrated antagonist activities toward 8-OH-DPAT-induced behavioral and electrophysiological responses in rats.

  DOI：

  10.1021/jm9707840
• 作为产物：
  描述：

  4-(4-甲氧基苯基)丁胺 在 lithium aluminium tetrahydride 、 碳酸氢钠 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 N-methyl-4-(4-methoxyphenyl)butylamine
  参考文献：
  名称：

  Synthesis and Pharmacological Characterization of Novel 6-Fluorochroman Derivatives as Potential 5-HT_1A Receptor Antagonists

  摘要：

  A series of novel 6-fluorochroman derivatives was prepared and evaluated as antagonists for the 5-HT1A receptor. N-2- [[(6-Fluorochroman-8-yl)oxy]ethyl]-4-(4-methoxyphenyl)butylamine (3; J. Med. Chem. 1997, 40, 1252-1257) was chosen as a lead, and structural modifications were done on the aliphatic portion of the chroman ring, the tether linking the middle amine and the terminal aromatic ring, the aromatic ring, and lastly the amine. Radioligand binding assays proved that the majority of the novel compounds behaved as good to excellent ligands at the 5-HT1A receptor, some of which were selective with respect to alpha(1)-adrenergic and D-2-dopaminergic receptors. The antagonist activity of the compounds was assessed in the forskolin-stimulated adenylate cyclase assays in CHO cells expressing the human 5-HT1A receptors. Among the modifications attempted, introduction of an oxo or an optically active hydroxy moiety at the chroman C-4 position was effective in ameliorating the receptor selectivity. Six analogues were selected through the in vitro screeds and further evaluated for their in vivo activities. A 4-oxochroman derivative (31n), having a terminal 1,3-benzodioxole ring, demonstrated antagonist activities toward 8-OH-DPAT-induced behavioral and electrophysiological responses in rats.

  DOI：

  10.1021/jm9707840

文献信息

• Synthesis and Pharmacological Characterization of Novel 6-Fluorochroman Derivatives as Potential 5-HT_1A Receptor Antagonists
  作者：Tomoyuki Yasunaga、Takenori Kimura、Ryo Naito、Toru Kontani、Fumikazu Wanibuchi、Hiroshi Yamashita、Tamako Nomura、Shin-ichi Tsukamoto、Tokio Yamaguchi、Toshiyasu Mase

  DOI：10.1021/jm9707840

  日期：1998.7.1

  A series of novel 6-fluorochroman derivatives was prepared and evaluated as antagonists for the 5-HT1A receptor. N-2- [[(6-Fluorochroman-8-yl)oxy]ethyl]-4-(4-methoxyphenyl)butylamine (3; J. Med. Chem. 1997, 40, 1252-1257) was chosen as a lead, and structural modifications were done on the aliphatic portion of the chroman ring, the tether linking the middle amine and the terminal aromatic ring, the aromatic ring, and lastly the amine. Radioligand binding assays proved that the majority of the novel compounds behaved as good to excellent ligands at the 5-HT1A receptor, some of which were selective with respect to alpha(1)-adrenergic and D-2-dopaminergic receptors. The antagonist activity of the compounds was assessed in the forskolin-stimulated adenylate cyclase assays in CHO cells expressing the human 5-HT1A receptors. Among the modifications attempted, introduction of an oxo or an optically active hydroxy moiety at the chroman C-4 position was effective in ameliorating the receptor selectivity. Six analogues were selected through the in vitro screeds and further evaluated for their in vivo activities. A 4-oxochroman derivative (31n), having a terminal 1,3-benzodioxole ring, demonstrated antagonist activities toward 8-OH-DPAT-induced behavioral and electrophysiological responses in rats.