tert-butyl 4-(m-tolylsulfonyl)-4,6,6a,7,9,10-hexahydro-8H-pyrazino[1,2-a]pyrrolo[4,3,2-de]quinoline-8-carboxylate | 1613592-90-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: tert-butyl 4-(m-tolylsulfonyl)-4,6,6a,7,9,10-hexahydro-8H-pyrazino[1,2-a]pyrrolo[4,3,2-de]quinoline-8-carboxylate
• CAS: 1613592-90-7
• 化学式: C₂₅H₂₉N₃O₄S
• 分子量: 467.589
• InChiKey: HTIORFIQLXXYTK-UHFFFAOYSA-N

物化性质

• 沸点：
  659.9±65.0 °C(predicted)
• 密度：
  1.33±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  33.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  71.85
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-(m-tolylsulfonyl)-4,6,6a,7,9,10-hexahydro-8H-pyrazino[1,2-a]pyrrolo[4,3,2-de]quinoline-8-carboxylate 在 盐酸 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 以58 mg的产率得到4-(m-tolylsulfonyl)-6,6a,7,8,9,10-hexahydro-4H-pyrazino[1,2-a]pyrrolo[4,3,2-de]quinoline
  参考文献：
  名称：

  Novel Aza-analogous Ergoline Derived Scaffolds as Potent Serotonin 5-HT₆ and Dopamine D₂ Receptor Ligands.

  摘要：

  By introducing distal substituents on a tetracyclic scaffold resembling the ergoline structure, two series of analogues were achieved exhibiting subnanomolar receptor binding affinities for the dopamine D-2 and serotonin S-HT6 receptor subtype, respectively. While the S-HT6 ligands were antagonists, the D-2 ligands displayed intrinsic activities ranging from full agonism to partial agonism with low intrinsic activity. These structures could potentially be interesting for treatment of neurological diseases such as schizophrenia, Parkinson's disease, and cognitive deficits.

  DOI：

  10.1021/jm5003759
• 作为产物：
  描述：

  tert-butyl 4-tosyl-6a,7,9,10-tetrahydro-4H-pyrazino[1,2-a]pyrrolo[4,3,2-de]quinoline-8(6H)-carboxylate 在 四丁基硫酸氢铵 、 magnesium 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 2.75h， 生成 tert-butyl 4-(m-tolylsulfonyl)-4,6,6a,7,9,10-hexahydro-8H-pyrazino[1,2-a]pyrrolo[4,3,2-de]quinoline-8-carboxylate
  参考文献：
  名称：

  Novel Aza-analogous Ergoline Derived Scaffolds as Potent Serotonin 5-HT₆ and Dopamine D₂ Receptor Ligands.

  摘要：

  By introducing distal substituents on a tetracyclic scaffold resembling the ergoline structure, two series of analogues were achieved exhibiting subnanomolar receptor binding affinities for the dopamine D-2 and serotonin S-HT6 receptor subtype, respectively. While the S-HT6 ligands were antagonists, the D-2 ligands displayed intrinsic activities ranging from full agonism to partial agonism with low intrinsic activity. These structures could potentially be interesting for treatment of neurological diseases such as schizophrenia, Parkinson's disease, and cognitive deficits.

  DOI：

  10.1021/jm5003759