N-methyl-N-propyl-N-(6,7,8,9-tetrahydro-3H-benz[e]indol-8-yl)amine | 163561-56-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: N-methyl-N-propyl-N-(6,7,8,9-tetrahydro-3H-benz[e]indol-8-yl)amine
• 英文别名: Methyl-propyl-(6,7,8,9-tetrahydro-3H-benzo[e]indol-8-yl)-amine；N-methyl-N-propyl-6,7,8,9-tetrahydro-3H-benzo[e]indol-8-amine
• CAS: 163561-56-6
• 化学式: C₁₆H₂₂N₂
• 分子量: 242.364
• InChiKey: WSLVLAZYRCUHNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  19
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-二甲基甲酰胺 、 N-methyl-N-propyl-N-(6,7,8,9-tetrahydro-3H-benz[e]indol-8-yl)amine 在 三氯氧磷 作用下， 以39%的产率得到8-(N-methyl-N-propylamino)-6,7,8,9-tetrahydro-3H-benz[e]indole-1-carbaldehyde
  参考文献：
  名称：

  Structure-Activity Relationships in the 8-Amino-6,7,8,9-tetrahydro-3H-benz[e]indole Ring System. Part 2: Effect of 8-Amino Nitrogen Substitution on Serotonin Receptor Binding and Pharmacology

  摘要：

  A series of analogs of the potent and selective 5-HT1A agonist 8-(di-n-propylamino)-6,7,8,9-tetrahydro-3H-benz[e]indole-1-carbaldehyde (2b) (OSU191) was prepared in which the dipropylamino group was modified to bear a variety of substituents. These compounds were evaluated for both in vitro and in vivo effects, including the establishment of a receptor binding profile for these analogs at the 5-HT1A, dopamine D-2, dopamine D-3, 5-HT1D alpha, and 5-HT1D beta sites. Several of the analogs were evaluated for their biochemical effects in reserpinized rats, specifically with regard to in vivo changes in brain levels of 5-HTP and DOPA. Nearly all of the compounds prepared for this study were exceedingly potent at the 5-HT1A receptor, although most also displayed significant affinity for the dopamine D-2 receptor. A strong preference for the 5-HT1D alpha, over the 5-HT1D beta receptor was also apparent. An analog bearing a butylglutarimide side chain, S-7k, was extremely selective for the 5-HT1A receptor. Although this compound possessed a K-i of 0.6 nM, it elicited only modest changes in 5-HTP brain levels. However, this compound did not appear as an antagonist when tested in a cyclic-AMP-based intrinsic activity assay.

  DOI：

  10.1021/jm00012a022
• 作为产物：
  描述：

  3-(p-toluenesulfonyl)-6,7,8,9-tetrahydro-3H-benzindol-8-one 在 sodium methylate 、 三乙酰氧基硼氢化钠 、 sodium cyanoborohydride 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 2.17h， 生成 N-methyl-N-propyl-N-(6,7,8,9-tetrahydro-3H-benz[e]indol-8-yl)amine
  参考文献：
  名称：

  Structure-Activity Relationships in the 8-Amino-6,7,8,9-tetrahydro-3H-benz[e]indole Ring System. Part 2: Effect of 8-Amino Nitrogen Substitution on Serotonin Receptor Binding and Pharmacology

  摘要：

  A series of analogs of the potent and selective 5-HT1A agonist 8-(di-n-propylamino)-6,7,8,9-tetrahydro-3H-benz[e]indole-1-carbaldehyde (2b) (OSU191) was prepared in which the dipropylamino group was modified to bear a variety of substituents. These compounds were evaluated for both in vitro and in vivo effects, including the establishment of a receptor binding profile for these analogs at the 5-HT1A, dopamine D-2, dopamine D-3, 5-HT1D alpha, and 5-HT1D beta sites. Several of the analogs were evaluated for their biochemical effects in reserpinized rats, specifically with regard to in vivo changes in brain levels of 5-HTP and DOPA. Nearly all of the compounds prepared for this study were exceedingly potent at the 5-HT1A receptor, although most also displayed significant affinity for the dopamine D-2 receptor. A strong preference for the 5-HT1D alpha, over the 5-HT1D beta receptor was also apparent. An analog bearing a butylglutarimide side chain, S-7k, was extremely selective for the 5-HT1A receptor. Although this compound possessed a K-i of 0.6 nM, it elicited only modest changes in 5-HTP brain levels. However, this compound did not appear as an antagonist when tested in a cyclic-AMP-based intrinsic activity assay.

  DOI：

  10.1021/jm00012a022