5,7-dichloro-3-hydroxy-2-oxo-1H-quinoline-4-carboxylic acid | 176170-08-4

• 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: 5,7-dichloro-3-hydroxy-2-oxo-1H-quinoline-4-carboxylic acid
• CAS: 176170-08-4
• 化学式: C₁₀H₅Cl₂NO₄
• 分子量: 274.06
• InChiKey: FYMAVFPHFBYNNM-UHFFFAOYSA-N

物化性质

• 沸点：
  463.7±45.0 °C(Predicted)
• 密度：
  1.812±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,7-dichloro-3-hydroxy-2-oxo-1H-quinoline-4-carboxylic acid 以 甲苯 为溶剂， 以100%的产率得到5,7-二氯-3-羟基喹啉-2(1h)-酮
  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
• 作为产物：
  描述：

  4,6-二氯靛红 在 盐酸 、 sodium hydroxide 、 二乙胺 作用下， 以 乙醇 、 水 为溶剂， 生成 5,7-dichloro-3-hydroxy-2-oxo-1H-quinoline-4-carboxylic acid
  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.