(E)-ethyl 3-(1-methyl-4-oxo-3-(2-(trifluoromethyl)biphenyl-4-ylcarbamoyl)-1,4-dihydroquinolin-7-yl)acrylate | 1351945-43-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-ethyl 3-(1-methyl-4-oxo-3-(2-(trifluoromethyl)biphenyl-4-ylcarbamoyl)-1,4-dihydroquinolin-7-yl)acrylate
• CAS: 1351945-43-1
• 化学式: C₂₉H₂₃F₃N₂O₄
• 分子量: 520.508
• InChiKey: JZFZPVQQKQLAOI-GXDHUFHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.05
• 重原子数：
  38.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  77.4
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 3-(1-methyl-4-oxo-3-(2-(trifluoromethyl)biphenyl-4-ylcarbamoyl)-1,4-dihydroquinolin-7-yl)acrylate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 72.0h， 以85%的产率得到ethyl 3-(1-methyl-4-oxo-3-(2-(trifluoromethyl)biphenyl-4-ylcarbamoyl)-1,4-dihydroquinolin-7-yl)propanoate
  参考文献：
  名称：

  Optimization of a Potent, Orally Active S1P₁ Agonist Containing a Quinolinone Core

  摘要：

  The optimization of a series of SIP, agonists with limited activity against S1P(3) is reported. A polar headgroup was used to improve the physicochemical and pharmacokinetic parameters of lead quinolinone 6. When dosed orally at 1 and 3 mg/kg, the azahydroxymethyl analogue 22 achieved statistically significant lowering of circulating blood lymphocytes 24 h postdose. In rats, a dose-proportional increase in exposure was measured when 22 was dosed orally at 2 and 100 mg/kg.

  DOI：

  10.1021/ml200252b
• 作为产物：
  描述：

  7-溴-4-羟基喹啉-3-甲酸乙酯 在 lithium hydroxide monohydrate 、 palladium diacetate 、 potassium carbonate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 (E)-ethyl 3-(1-methyl-4-oxo-3-(2-(trifluoromethyl)biphenyl-4-ylcarbamoyl)-1,4-dihydroquinolin-7-yl)acrylate
  参考文献：
  名称：

  Optimization of a Potent, Orally Active S1P₁ Agonist Containing a Quinolinone Core

  摘要：

  The optimization of a series of SIP, agonists with limited activity against S1P(3) is reported. A polar headgroup was used to improve the physicochemical and pharmacokinetic parameters of lead quinolinone 6. When dosed orally at 1 and 3 mg/kg, the azahydroxymethyl analogue 22 achieved statistically significant lowering of circulating blood lymphocytes 24 h postdose. In rats, a dose-proportional increase in exposure was measured when 22 was dosed orally at 2 and 100 mg/kg.

  DOI：

  10.1021/ml200252b