(S)-5-<3-(2-quinolinylmethoxy)phenyl>-3-methyl-2-oxazolidone | 110193-40-3

• 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: (S)-5-<3-(2-quinolinylmethoxy)phenyl>-3-methyl-2-oxazolidone
• 英文别名: WY-48185；(S)-5-[3-(2-quinolinylmethoxy)phenyl]-3-methyl-2-oxazolidone；(5S)-3-methyl-5-[3-(quinolin-2-ylmethoxy)phenyl]-1,3-oxazolidin-2-one
• CAS: 110193-40-3
• 化学式: C₂₀H₁₈N₂O₃
• 分子量: 334.375
• InChiKey: CJBINGOMISUGEU-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  51.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯肾上腺素杂质 在 potassium carbonate 、 caesium carbonate 作用下， 以 丙酮 为溶剂， 反应 52.0h， 生成 (S)-5-<3-(2-quinolinylmethoxy)phenyl>-3-methyl-2-oxazolidone
  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

• MUSSER, JOHN H.;KUBRAK, DENNIS M.;BENDER, REINHOLD H. W.;KREFT, ANTHONY F+, J. MED. CHEM., 30,(1987) N 11, 2087-2093
  作者：MUSSER, JOHN H.、KUBRAK, DENNIS M.、BENDER, REINHOLD H. W.、KREFT, ANTHONY F+

  DOI：——

  日期：——
• MUSSER, JOHN H.;BENDER, REINHOLD H. W.
  作者：MUSSER, JOHN H.、BENDER, REINHOLD H. W.

  DOI：——

  日期：——
• NOGO RECEPTOR FUNCTIONAL MOTIFS, PEPTIDE MIMETICS, AND MUTATED FUNCTIONAL MOTIFS RELATED THERETO, AND METHODS OF USING THE SAME
  申请人：Wood Andrew

  公开号：US20080027001A1

  公开（公告）日：2008-01-31

  The present invention provides novel isolated and purified polynucleotides and polypeptides related to functional motifs of the Nogo receptor 1 (NgR1) (e.g., the binding pocket on the side surface of NgR1, functional motifs comprising the amino acid sequence of FRG, etc.) and use of peptides mimicking these functional motifs as antagonists to NgR1 ligands, e.g., myelin-associated glycoprotein, oligodendrocyte myelin glycoprotein, Nogo-A, Nogo-66, GT1 b , an antibody to Nogo receptor, an antibody to GT1 b , an antibody to p75 neurotrophin receptor, and an antibody to Lingo-1, etc. The invention also provides antibodies to the mimetic peptide antagonists. The present invention is further directed to novel therapeutics and therapeutic targets and to methods of screening and assessing test compounds for treatments requiring axonal regeneration, i.e., reversal of the effects of NgR1 ligand binding to the NgR1 (i.e., producing inhibition of axonal growth). The present invention also is directed to novel methods for treating disorders arising from inhibition of axonal growth mediated by the binding of NgR1 ligands to the NgR1. Further, the invention is directed to methods of treating a subject with a neurodegenerative disorder, including, but not limited to, Parkinson's disease, Alzheimer's disease, progressive supranuclear palsy, multiple sclerosis, multiple system atrophy, corticobasal degeneration, Huntington's disease, dementia with Lewy bodies, spinocerebellar ataxia, stroke, spinal cord trauma, traumatic brain injury, multiinfarct dementia, epilepsy, and senile dementia, comprising, e.g., antagonizing NgR1.
• 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.