2,3,4,9-tetrahydro-2-[3-(3-pyridinyl)propyl]-1H-pyrido[3,4-b]indole | 114478-30-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2,3,4,9-tetrahydro-2-[3-(3-pyridinyl)propyl]-1H-pyrido[3,4-b]indole
• 英文别名: 2-(3-Pyridin-3-yl-propyl)-2,3,4,9-tetrahydro-1H-beta-carboline；2-(3-pyridin-3-ylpropyl)-1,3,4,9-tetrahydropyrido[3,4-b]indole
• CAS: 114478-30-7
• 化学式: C₁₉H₂₁N₃
• 分子量: 291.396
• InChiKey: OPKWRJFGFHYVMY-UHFFFAOYSA-N

物化性质

• 沸点：
  495.2±45.0 °C(predicted)
• 密度：
  1.176±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  31.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-二甲氨基氯丙烷盐酸盐 、 2,3,4,9-tetrahydro-2-[3-(3-pyridinyl)propyl]-1H-pyrido[3,4-b]indole 在 sodium hydride 作用下， 生成 Dimethyl-{3-[2-(3-pyridin-3-yl-propyl)-1,2,3,4-tetrahydro-β-carbolin-9-yl]-propyl}-amine
  参考文献：
  名称：

  Psychotropic agents: synthesis and antipsychotic activity of substituted .beta.-carbolines

  摘要：

  A series of novel substituted beta-carbolines was synthesized and tested for potential antipsychotic activity. Several compounds displayed moderate antipsychotic activity in vitro and in vivo as determined by relevant receptor binding assays and behavioral tests. The effect of substituents on antipsychotic activity was examined. The beta-carbolines 10 and 19 containing 2-(2-pyridinyl)ethyl and 2-(2-quinolinyl)ethyl side chains were the most potent analogues, blocking discrete trial conditioned avoidance responding in rats with AB50's of 23 and 10 mg/kg, respectively. Both showed moderate activity at the D2 receptor sites, but they lacked oral activity. In contrast, the beta-carboline 13 containing the 4-(4-pyridinyl)butyl side chain exhibited oral activity in the discrete trial conditioned avoidance screen with an AB50 of 31 mg/kg. Most compounds did not antagonize apomorphine-induced stereotyped behavior, which is indicative of low potential for extrapyramidal side effect (EPS) liability.

  DOI：

  10.1021/jm00389a022
• 作为产物：
  描述：

  3-(3-Phenoxypropyl)pyridine 在 氢溴酸 、 potassium carbonate 、 caesium carbonate 、 potassium iodide 作用下， 反应 1.0h， 生成 2,3,4,9-tetrahydro-2-[3-(3-pyridinyl)propyl]-1H-pyrido[3,4-b]indole
  参考文献：
  名称：

  Psychotropic agents: synthesis and antipsychotic activity of substituted .beta.-carbolines

  摘要：

  A series of novel substituted beta-carbolines was synthesized and tested for potential antipsychotic activity. Several compounds displayed moderate antipsychotic activity in vitro and in vivo as determined by relevant receptor binding assays and behavioral tests. The effect of substituents on antipsychotic activity was examined. The beta-carbolines 10 and 19 containing 2-(2-pyridinyl)ethyl and 2-(2-quinolinyl)ethyl side chains were the most potent analogues, blocking discrete trial conditioned avoidance responding in rats with AB50's of 23 and 10 mg/kg, respectively. Both showed moderate activity at the D2 receptor sites, but they lacked oral activity. In contrast, the beta-carboline 13 containing the 4-(4-pyridinyl)butyl side chain exhibited oral activity in the discrete trial conditioned avoidance screen with an AB50 of 31 mg/kg. Most compounds did not antagonize apomorphine-induced stereotyped behavior, which is indicative of low potential for extrapyramidal side effect (EPS) liability.

  DOI：

  10.1021/jm00389a022

文献信息

• US4719211A
  申请人：——

  公开号：US4719211A

  公开（公告）日：1988-01-12