(R)-N-ethylnorphenylephrine | 2259-99-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (R)-N-ethylnorphenylephrine
• 英文别名: (R)-etilefrine；etilefrin；Etilefrine, (R)-；3-[(1R)-2-(ethylamino)-1-hydroxyethyl]phenol
• CAS: 2259-99-6
• 化学式: C₁₀H₁₅NO₂
• 分子量: 181.235
• InChiKey: SQVIAVUSQAWMKL-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  52.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  乙苯福林 生成 (R)-N-ethylnorphenylephrine 、 (S)-etilefrine
  参考文献：
  名称：

  Schmid; Wirnsberger; Guebitz, Pharmazie, 1996, vol. 51, # 11, p. 852 - 854

  摘要：

  DOI：

文献信息

• Formation of a direct mutagen, diazo-N-nitrosoetilefrin, by interaction of etilefrin with nitrite.
  作者：Kiyomi KIKUGAWA、Teshuta KATO、Yasushi TAKEDA

  DOI：10.1248/cpb.37.1600

  日期：——

  drug, etilefrin [alpha-[(ethylamino)methyl]-m-hydroxybenzyl alcohol], with nitrite under mildly acidic conditions produced N-nitrosoetilefrin [alpha-[(N-nitrosoethylamino)methyl]-m-hydroxybenzyl alcohol] (a mixture of syn and anti forms) (Iab) and diazo-N-nitrosoetilefrin [1-(4-diazo-3-oxo-1,5-cyclohexadienyl-2-(N-nitrosoethylamino )ethanol] (a mixture of syn and anti forms) (IIab). Treatment of etilefrin

  化合物IIab对鼠伤寒沙门氏菌TA98和TA100菌株表现出致突变性，而没有代谢活化。对于TA98和TA100菌株，IIab的特异性诱变活性均为300 his +回复菌落，剂量为0.1μmol。添加微粒体激活系统对活性几乎没有影响。值得注意的是，该口服药物可通过与消化道中存在的亚硝酸盐反应而产生直接作用的诱变剂。
• 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.
• Schmid; Wirnsberger; Guebitz, Pharmazie, 1996, vol. 51, # 11, p. 852 - 854
  作者：Schmid、Wirnsberger、Guebitz

  DOI：——

  日期：——