5-Butylamino-5,6-dihydro-1H,4H-imidazo[4,5,1-ij]quinolin-2-one | 139525-61-4

• 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: 5-Butylamino-5,6-dihydro-1H,4H-imidazo[4,5,1-ij]quinolin-2-one
• 英文别名: 10-(butylamino)-1,3-diazatricyclo[6.3.1.04,12]dodeca-4,6,8(12)-trien-2-one
• CAS: 139525-61-4
• 化学式: C₁₄H₁₉N₃O
• 分子量: 245.324
• InChiKey: NRLIHXRPOFGROM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  tert-butyl (8-amino-1,2,3,4-tetrahydro-3-quinolinyl)carbamate 在 盐酸 、 sodium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.08h， 生成 5-Butylamino-5,6-dihydro-1H,4H-imidazo[4,5,1-ij]quinolin-2-one
  参考文献：
  名称：

  Dopaminergic and serotonergic activities of imidazoquinolinones and related compounds

  摘要：

  The synthesis of 5-(dipropylamino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one (5), a potent dopamine D2 agonist showing high dopamine/serotonin (5HT1A) selectivity, is described. Dopaminergic activity is associated with the (R)-enantiomer of 5; the (S)-enantiomer shows no dopaminergic activity. A series of analogues where the imidazolone ring was modified to various 5- or 6-membered heterocyclic rings were prepared. Some of these compounds showed a combination of dopaminergic and serotonergic activity, while one compound, 6-(dipropylamino)-1,2,6,7-tetrahydro-3H,5H-pyrido[3,2,1-ij]quinazolin-3-one (24), was a selective serotonergic agonist. Various analogues of 5 where the dipropylamine substituent was modified were prepared. Most of these showed reduced dopaminergic activity, while several were as potent as 5 at the serotonin 5HT1A receptor. Orientations for the new compounds at dopamine and serotonin receptors are proposed and compared with those of other tricyclic ligands known to have high affinity at these receptors.

  DOI：

  10.1021/jm00084a013

文献信息

• Dopaminergic and serotonergic activities of imidazoquinolinones and related compounds
  作者：Malcolm W. Moon、Jeanette K. Morris、Richard F. Heier、Connie G. Chidester、William E. Hoffmann、Montford F. Piercey、John S. Althaus、Philip F. VonVoigtlander、Dawna L. Evans

  DOI：10.1021/jm00084a013

  日期：1992.3

  The synthesis of 5-(dipropylamino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one (5), a potent dopamine D2 agonist showing high dopamine/serotonin (5HT1A) selectivity, is described. Dopaminergic activity is associated with the (R)-enantiomer of 5; the (S)-enantiomer shows no dopaminergic activity. A series of analogues where the imidazolone ring was modified to various 5- or 6-membered heterocyclic rings were prepared. Some of these compounds showed a combination of dopaminergic and serotonergic activity, while one compound, 6-(dipropylamino)-1,2,6,7-tetrahydro-3H,5H-pyrido[3,2,1-ij]quinazolin-3-one (24), was a selective serotonergic agonist. Various analogues of 5 where the dipropylamine substituent was modified were prepared. Most of these showed reduced dopaminergic activity, while several were as potent as 5 at the serotonin 5HT1A receptor. Orientations for the new compounds at dopamine and serotonin receptors are proposed and compared with those of other tricyclic ligands known to have high affinity at these receptors.