ethyl 5,7-dichloro-3-hydroxy-2-oxo-1H-quinoline-4-carboxylate | 176170-05-1

• 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: ethyl 5,7-dichloro-3-hydroxy-2-oxo-1H-quinoline-4-carboxylate
• CAS: 176170-05-1
• 化学式: C₁₂H₉Cl₂NO₄
• 分子量: 302.114
• InChiKey: RZXBBYPSUNEEEG-UHFFFAOYSA-N

物化性质

• 沸点：
  504.2±50.0 °C(Predicted)
• 密度：
  1.564±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 5,7-dichloro-3-hydroxy-2-oxo-1H-quinoline-4-carboxylate 在 盐酸 、 四(三苯基膦)钯 、 四丁基氯化铵 、 二异丁基氢化铝 、 caesium carbonate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， -70.0~110.0 ℃ 、344.74 kPa 条件下， 生成 (5,7-Dichloro-3-hydroxy-2-oxo-1,2-dihydro-quinolin-4-yl)-acetic acid methyl ester
  参考文献：
  名称：

  Fray, M. Jonathan; Bull, David J.; Carr, Christopher L., Medicinal Chemistry Research, 1996, vol. 6, # 9, p. 581 - 592

  摘要：

  DOI：
• 作为产物：
  描述：

  4,6-二氯靛红 在 盐酸 、 二乙胺 作用下， 以 乙醇 、 水 为溶剂， 生成 ethyl 5,7-dichloro-3-hydroxy-2-oxo-1H-quinoline-4-carboxylate
  参考文献：
  名称：

  3-Hydroxy-quinolin-2-ones: Inhibitors of [3H]-glycine binding to the site associated with the NMDA receptor

  摘要：

  A series of substituted 3-hydroxy-quinolin-2-one derivatives 6 was synthesized and evaluated as inhibitors of [H-3]-glycine and [H-3]-AMPA binding to rat cortical membranes. These compounds were generally found to be more potent ligands for the NMDA-associated glycine binding site than the AMPA receptor. Affinity for the glycine site was found to be influenced by both the electronic and steric properties associated with the C-4 substituent and the nature and pattern of substitution of the aromatic ring. The most active compound in this series, 6y, displaces [H-3]-glycine with an IC50 of 29 nM.

  DOI：

  10.1016/0960-894x(96)00031-5

文献信息

• 3-Hydroxy-quinolin-2-ones: Inhibitors of [3H]-glycine binding to the site associated with the NMDA receptor
  作者：Sing-Yuen Sit、Frederick J. Ehrgott、Jinnian Gao、Nicholas A. Meanwell

  DOI：10.1016/0960-894x(96)00031-5

  日期：1996.3

  A series of substituted 3-hydroxy-quinolin-2-one derivatives 6 was synthesized and evaluated as inhibitors of [H-3]-glycine and [H-3]-AMPA binding to rat cortical membranes. These compounds were generally found to be more potent ligands for the NMDA-associated glycine binding site than the AMPA receptor. Affinity for the glycine site was found to be influenced by both the electronic and steric properties associated with the C-4 substituent and the nature and pattern of substitution of the aromatic ring. The most active compound in this series, 6y, displaces [H-3]-glycine with an IC50 of 29 nM.
• Fray, M. Jonathan; Bull, David J.; Carr, Christopher L., Medicinal Chemistry Research, 1996, vol. 6, # 9, p. 581 - 592
  作者：Fray, M. Jonathan、Bull, David J.、Carr, Christopher L.、Stobie, Alan

  DOI：——

  日期：——