1-methyl-4-oxo-7-(3-oxopropyl)-N-(2-(trifluoromethyl)biphenyl-4-yl)-1,4-dihydroquinoline-3-carboxamide | 1351945-39-5

• 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: 1-methyl-4-oxo-7-(3-oxopropyl)-N-(2-(trifluoromethyl)biphenyl-4-yl)-1,4-dihydroquinoline-3-carboxamide
• CAS: 1351945-39-5
• 化学式: C₂₇H₂₁F₃N₂O₃
• 分子量: 478.471
• InChiKey: DPCHANPUINWLKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.61
• 重原子数：
  35.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  68.17
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-methyl-4-oxo-7-(3-oxopropyl)-N-(2-(trifluoromethyl)biphenyl-4-yl)-1,4-dihydroquinoline-3-carboxamide 在 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 0.5h， 以46%的产率得到7-(3-hydroxypropyl)-1-methyl-4-oxo-N-(2-(trifluoromethyl)-4-biphenylyl)-1,4-dihydro-3-quinolinecarboxamide
  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 、 苄基三乙基氯化铵 、 palladium diacetate 、 potassium carbonate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 1-methyl-4-oxo-7-(3-oxopropyl)-N-(2-(trifluoromethyl)biphenyl-4-yl)-1,4-dihydroquinoline-3-carboxamide
  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