9-amino-2-cyclobutyl-5-(pyrimidin-5-yl)-2,3-dihydro-1Hpyrrolo[3,4-b]quinolin-1-one | 1261980-48-6

• 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: 9-amino-2-cyclobutyl-5-(pyrimidin-5-yl)-2,3-dihydro-1Hpyrrolo[3,4-b]quinolin-1-one
• 英文别名: 9-amino-2-cyclobutyl-5-pyrimidin-5-yl-3H-pyrrolo[3,4-b]quinolin-1-one
• CAS: 1261980-48-6
• 化学式: C₁₉H₁₇N₅O
• 分子量: 331.377
• InChiKey: PEEGZDFBOLCRFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  85
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  9-amino-5-bromo-2-cyclobutyl-2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-1-one 、 5-嘧啶硼酸 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 乙二醇二甲醚 、 乙醇 、 水 为溶剂， 反应 2.0h， 以77%的产率得到9-amino-2-cyclobutyl-5-(pyrimidin-5-yl)-2,3-dihydro-1Hpyrrolo[3,4-b]quinolin-1-one
  参考文献：
  名称：

  Developing dual functional allosteric modulators of GABAA receptors

  摘要：

  Positive modulators at benzodiazepine sites of alpha 2- and alpha 3-containing GABA(A) receptors are believed to be anxiolytic. Negative allosteric modulators of alpha 5-containing GABA(A) receptors enhance cognition. By oocyte two-electrode voltage clamp and subsequent structure-activity relationship studies, we discovered cinnoline and quinoline derivatives that were both positive modulators at alpha 2-/alpha 3-containing GABA(A) receptors and negative modulators at alpha 5-containing GABA(A) receptors. In addition, these compounds showed no functional activity at alpha 1-containing GABA(A) receptors. Such dual functional modulators of GABA(A) receptors might be useful for treating comorbidity of anxiety and cognitive impairments in neurological and psychiatric illnesses. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.058

文献信息

• Developing dual functional allosteric modulators of GABAA receptors
  作者：Xiaodong F. Liu、Hui-Fang Chang、Richard Jon Schmiesing、Steven S. Wesolowski、Katharine S. Knappenberger、Jeffrey L. Arriza、Marc J. Chapdelaine

  DOI：10.1016/j.bmc.2010.09.058

  日期：2010.12

  Positive modulators at benzodiazepine sites of alpha 2- and alpha 3-containing GABA(A) receptors are believed to be anxiolytic. Negative allosteric modulators of alpha 5-containing GABA(A) receptors enhance cognition. By oocyte two-electrode voltage clamp and subsequent structure-activity relationship studies, we discovered cinnoline and quinoline derivatives that were both positive modulators at alpha 2-/alpha 3-containing GABA(A) receptors and negative modulators at alpha 5-containing GABA(A) receptors. In addition, these compounds showed no functional activity at alpha 1-containing GABA(A) receptors. Such dual functional modulators of GABA(A) receptors might be useful for treating comorbidity of anxiety and cognitive impairments in neurological and psychiatric illnesses. (C) 2010 Elsevier Ltd. All rights reserved.