ethyl 3-(1-methyl-4-oxo-3-(2-(trifluoromethyl)biphenyl-4-ylcarbamoyl)-1,4-dihydro-1,6-naphthyridin-7-yl)propanoate | 1351945-47-5

• 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: ethyl 3-(1-methyl-4-oxo-3-(2-(trifluoromethyl)biphenyl-4-ylcarbamoyl)-1,4-dihydro-1,6-naphthyridin-7-yl)propanoate
• CAS: 1351945-47-5
• 化学式: C₂₈H₂₄F₃N₃O₄
• 分子量: 523.511
• InChiKey: LIQJJIMAEXSZLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.37
• 重原子数：
  38.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  90.29
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl 3-(1-methyl-4-oxo-3-(2-(trifluoromethyl)biphenyl-4-ylcarbamoyl)-1,4-dihydro-1,6-naphthyridin-7-yl)propanoate 在 potassium hydroxide 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 1.0h， 以77%的产率得到3-(1-methyl-4-oxo-3-(2-(trifluoromethyl)biphenyl-4-ylcarbamoyl)-1,4-dihydro-1,6-naphthyridin-7-yl)propanoic acid
  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-formyl-1-methyl-4-oxo-N-(2-(trifluoromethyl)biphenyl-4-yl)-1,4-dihydroquinoline-3-carboxamide 在 磷酰基乙酸三乙酯 、 palladium 10% on activated carbon 、 1,8-diazabicyclo[5.4.0] undec-7-ene 、 氢气 、 lithium chloride 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 9.0h， 生成 ethyl 3-(1-methyl-4-oxo-3-(2-(trifluoromethyl)biphenyl-4-ylcarbamoyl)-1,4-dihydro-1,6-naphthyridin-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