3-phenylquinoline-2,8-dicarboxylic acid

• 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: 3-phenylquinoline-2,8-dicarboxylic acid
• 化学式: C₁₇H₁₁NO₄
• 分子量: 293.279
• InChiKey: KSRONUPGURAQJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-phenylquinoline-2,8-dicarboxylic acid 在 PPA 作用下， 反应 1.0h， 生成 6-oxo-6H-indeno[2,1-b]quinoline-4-carboxylic acid
  参考文献：
  名称：

  摘要：

  The acid precursors of the title compounds were prepared from methyl 2-amino-3-formylbenzoate (3), by Friedlander synthesis with o-methoxy- and o-nitro-phenylacetic acids, phenylpyruvic acid and benzo[b]thiophen-2-one, respectively. Except for the last example, cyclization of an initial 3-arylquinoline derivative was then required to give the tetracycle. Growth inhibition properties of the carboxamides in a series of cancer cell lines were measured for comparison with previous data for an isomeric series. In all cases, the present set were found to be less active.

  DOI：

  10.1071/ch99166
• 作为产物：
  描述：

  苯丙酮酸 、 2-氨基-3-羧酸甲酯苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以80%的产率得到3-phenylquinoline-2,8-dicarboxylic acid
  参考文献：
  名称：

  摘要：

  The acid precursors of the title compounds were prepared from methyl 2-amino-3-formylbenzoate (3), by Friedlander synthesis with o-methoxy- and o-nitro-phenylacetic acids, phenylpyruvic acid and benzo[b]thiophen-2-one, respectively. Except for the last example, cyclization of an initial 3-arylquinoline derivative was then required to give the tetracycle. Growth inhibition properties of the carboxamides in a series of cancer cell lines were measured for comparison with previous data for an isomeric series. In all cases, the present set were found to be less active.

  DOI：

  10.1071/ch99166

文献信息

• ——
  作者：Xianyong Bu、Leslie W. Deady、William A. Denny

  DOI：10.1071/ch99166

  日期：——

  The acid precursors of the title compounds were prepared from methyl 2-amino-3-formylbenzoate (3), by Friedlander synthesis with o-methoxy- and o-nitro-phenylacetic acids, phenylpyruvic acid and benzo[b]thiophen-2-one, respectively. Except for the last example, cyclization of an initial 3-arylquinoline derivative was then required to give the tetracycle. Growth inhibition properties of the carboxamides in a series of cancer cell lines were measured for comparison with previous data for an isomeric series. In all cases, the present set were found to be less active.