1-methyl-4-oxo-N-[4-phenyl-3-(trifluoromethyl)phenyl]quinoline-3-carboxamide | 1351945-07-7

• 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-N-[4-phenyl-3-(trifluoromethyl)phenyl]quinoline-3-carboxamide
• CAS: 1351945-07-7
• 化学式: C₂₄H₁₇F₃N₂O₂
• 分子量: 422.406
• InChiKey: XRRCRIQWBWQWDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-(trifluoromethyl)biphenyl-4-amine 、 1-甲基-4-氧代-1,4-二氢喹啉-3-羧酸 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以62%的产率得到1-methyl-4-oxo-N-[4-phenyl-3-(trifluoromethyl)phenyl]quinoline-3-carboxamide
  参考文献：
  名称：

  Quinolinone-based agonists of S1P1: Use of a N-scan SAR strategy to optimize in vitro and in vivo activity

  摘要：

  We reveal how a N-scan SAR strategy (systematic substitution of each CH group with a N atom) was employed for quinolinone-based S1P(1) agonist 5 to modulate physicochemical properties and optimize in vitro and in vivo activity. The diaza-analog 17 displays improved potency (hS1P(1) RI; 17: EC50 = 0.020 mu M, 120% efficacy; 5: EC50 = 0.070 mu M, 110% efficacy) and selectivity (hS1P(3) Ca2+ flux; 17: EC50 >25 mu M; 5: EC50 = 1.5 mu M, 92% efficacy), as well as enhanced pharmacokinetics (17: CL = 0.15 L/h/kg, V-dss = 5.1 L/kg, T-1/2 = 24 h, % F = 110; 5: CL = 0.93 L/h/kg, V-dss = 11 L/kg, T-1/2 = 15 h, % F = 60) and pharmacodynamics (17: 1.0 mg/kg po, 24 h PLC POC = -67%; 5: 3 mg/kg po, 24 h PLC POC = -51%) in rat. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.085