7-[2-(4-溴苯氧基)乙氧基]-4-氧代-1H-喹啉-3-羧酸 | 78105-16-5

• 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
• 中文名称: 7-[2-(4-溴苯氧基)乙氧基]-4-氧代-1H-喹啉-3-羧酸
• 英文名称: 7-[2-(4-bromophenoxy)ethoxy]-4-oxo-1H-quinoline-3-carboxylic acid
• CAS: 78105-16-5
• 化学式: C₁₈H₁₄BrNO₅
• 分子量: 404.217
• InChiKey: GKSJNZMDNQSZMN-UHFFFAOYSA-N

物化性质

• 沸点：
  596.0±50.0 °C(Predicted)
• 密度：
  1.598±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-(2-溴氧基)-4-溴苯 在 盐酸 、 sodium hydroxide 、 sodium 、 tin(ll) chloride 作用下， 以 二苯醚 、 乙醇 、 甲苯 为溶剂， 反应 30.13h， 生成 7-[2-(4-溴苯氧基)乙氧基]-4-氧代-1H-喹啉-3-羧酸
  参考文献：
  名称：

  4-Hydroxyquinoline-3-carboxylic acids as inhibitors of cell respiration. 2. Quantitative structure-activity relationship of dehydrogenase enzyme and Ehrlich ascites tumor cell inhibitions

  摘要：

  Studies on dehydrogenase enzyme inhibition have been extended with the design, synthesis, and correlation analysis of 7-[(substituted-benzyl)oxy]-, 7-[(substituted-phenethyl)oxy]-, and 7([substituted-phenoxy)ethoxy]-4-hydroxyquinoline-3-carboxylic acids. Sixteen new congeners and the fifteen molecules previously synthesized have been tested against cytoplasmic malate dehydrogenase and lactate dehydrogenase, as well as against mitochondrial malate dehydrogenase. The lipophilic congeners show a clear specificity for inhibition of the mitochondrial enzyme. Correlation analysis of the data on the three enzymes allows a comparison of the binding sites in quantitative terms, while examination of the data on inhibition of ascites tumor cell respiration affords an indication of membrane transport. A newly developed high-pressure liquid chromatography based retention index is compared to the octanol-water pi constant as a model for hydrophobic interactions.

  DOI：

  10.1021/jm00343a011

文献信息

• 4-Hydroxyquinoline-3-carboxylic acids as inhibitors of cell respiration. 2. Quantitative structure-activity relationship of dehydrogenase enzyme and Ehrlich ascites tumor cell inhibitions
  作者：Eugene A. Coats、Kishorkant J. Shah、Stanley R. Milstein、Clara S. Genther、Dilip M. Nene、Jeffrey Roesener、James Schmidt、Michael Pleiss、Ellen Wagner、John K. Baker

  DOI：10.1021/jm00343a011

  日期：1982.1

  Studies on dehydrogenase enzyme inhibition have been extended with the design, synthesis, and correlation analysis of 7-[(substituted-benzyl)oxy]-, 7-[(substituted-phenethyl)oxy]-, and 7([substituted-phenoxy)ethoxy]-4-hydroxyquinoline-3-carboxylic acids. Sixteen new congeners and the fifteen molecules previously synthesized have been tested against cytoplasmic malate dehydrogenase and lactate dehydrogenase, as well as against mitochondrial malate dehydrogenase. The lipophilic congeners show a clear specificity for inhibition of the mitochondrial enzyme. Correlation analysis of the data on the three enzymes allows a comparison of the binding sites in quantitative terms, while examination of the data on inhibition of ascites tumor cell respiration affords an indication of membrane transport. A newly developed high-pressure liquid chromatography based retention index is compared to the octanol-water pi constant as a model for hydrophobic interactions.