(1R)-1-[3-[(2-quinolinyl)methoxy]phenyl]-2-(N-ethyl-N-diethylcarbamoyl)amino ethanol | 110205-28-2

• 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: (1R)-1-[3-[(2-quinolinyl)methoxy]phenyl]-2-(N-ethyl-N-diethylcarbamoyl)amino ethanol
• 英文别名: 1,1,3-triethyl-3-[(2R)-2-hydroxy-2-[3-(quinolin-2-ylmethoxy)phenyl]ethyl]urea
• CAS: 110205-28-2
• 化学式: C₂₅H₃₁N₃O₃
• 分子量: 421.539
• InChiKey: POFHKEAFXBKLTJ-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  65.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (R)-N-ethylnorphenylephrine 在 caesium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 49.0h， 生成 (1R)-1-[3-[(2-quinolinyl)methoxy]phenyl]-2-(N-ethyl-N-diethylcarbamoyl)amino ethanol
  参考文献：
  名称：

  Phenylephrine derivatives as leukotriene D4 antagonists

  摘要：

  Two series of phenylephrine derivatives were prepared and tested as inhibitors of leukotriene D4 (LTD4) induced and ovalbumin-induced bronchospasm in the guinea pig. The most potent compound of the urea series, (R)-N,N-diethyl-N-[2-hydroxy-2-[3-(2-quinolinylmethoxy)phenyl]ethyl]-N- methylurea (3, Wy-47,120), was orally active with ED50's of 56 mg/kg vs. LTD4 and 55 mg/kg vs. ovalbumin. When tested as an antagonist of LTD4-induced contraction of isolated guinea pig tracheal strips, 3 was a competitive inhibitor with a p kappa B value of 5.22. In the second series, (R)-3-methyl-5-[3-(2-quinolinylmethoxy)phenyl]-2-oxazolidinone (26, Wy-47,674) had oral ED50's of 36 mg/kg against LTD4 and 95 mg/kg against ovalbumin. Compound 26 selectively antagonized contractile responses of guinea pig trachea evoked by LTD4 (p kappa B = 6.09). In the cat coronary artery, 3 dilated the preparation and blocked the coronary constrictor effect of LTD4. Compound 3 (0.13 mg/kg, iv) also preserved myocardial integrity in rats 48 h after coronary artery ligation. When tested in the rat alcohol-induced gastric lesion model, 3 and 26 manifested a dose-dependent mucosal protection against ethanol.

  DOI：

  10.1021/jm00394a026

文献信息

• US4876346A
  申请人：——

  公开号：US4876346A

  公开（公告）日：1989-10-24
• Phenylephrine derivatives as leukotriene D4 antagonists
  作者：John H. Musser、Dennis M. Kubrak、Reinhold H. W. Bender、Anthony F. Kreft、Susan T. Nielsen、Allan M. Lefer、Joseph Chang、Alan J. Lewis、James M. Hand

  DOI：10.1021/jm00394a026

  日期：1987.11

  Two series of phenylephrine derivatives were prepared and tested as inhibitors of leukotriene D4 (LTD4) induced and ovalbumin-induced bronchospasm in the guinea pig. The most potent compound of the urea series, (R)-N,N-diethyl-N-[2-hydroxy-2-[3-(2-quinolinylmethoxy)phenyl]ethyl]-N- methylurea (3, Wy-47,120), was orally active with ED50's of 56 mg/kg vs. LTD4 and 55 mg/kg vs. ovalbumin. When tested as an antagonist of LTD4-induced contraction of isolated guinea pig tracheal strips, 3 was a competitive inhibitor with a p kappa B value of 5.22. In the second series, (R)-3-methyl-5-[3-(2-quinolinylmethoxy)phenyl]-2-oxazolidinone (26, Wy-47,674) had oral ED50's of 36 mg/kg against LTD4 and 95 mg/kg against ovalbumin. Compound 26 selectively antagonized contractile responses of guinea pig trachea evoked by LTD4 (p kappa B = 6.09). In the cat coronary artery, 3 dilated the preparation and blocked the coronary constrictor effect of LTD4. Compound 3 (0.13 mg/kg, iv) also preserved myocardial integrity in rats 48 h after coronary artery ligation. When tested in the rat alcohol-induced gastric lesion model, 3 and 26 manifested a dose-dependent mucosal protection against ethanol.