10H-indolo[3,2-b]quinoline-9-carboxylic acid | 1346173-71-4

• 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: 10H-indolo[3,2-b]quinoline-9-carboxylic acid
• CAS: 1346173-71-4
• 化学式: C₁₆H₁₀N₂O₂
• 分子量: 262.268
• InChiKey: DNUJAGMMQHRREO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(2-溴乙酰氨基)苯甲酸甲酯 在 palladium on activated charcoal 、 氢气 、 三乙胺 、 potassium hydroxide 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 66.0h， 生成 10H-indolo[3,2-b]quinoline-9-carboxylic acid
  参考文献：
  名称：

  Synthesis, Saccharide-Binding and Anti-cancer Cell Proliferation Properties of Arylboronic Acid Derivatives of Indoquinolines

  摘要：

  A facile synthesis of a series of saccharide‐binding arylboronic acid derivatives of indoloquinoline was described. The key synthetic steps were polyphosphoric acid‐mediated cyclization, chlorinative aromatization, and amidation. Mass spectrometry experiments revealed these synthetic arylboronic acid derivatives of indoquinolines could bind to biologically important carbohydrates (sialic acid, fucose, glucose, and galactose) by forming boronate di‐esters in alkaline aqueous solution. Most of the arylboronic acid derivatives of indoquinolines inhibited human breast cancer cell (MDA–231) proliferation at a concentration of 5 μm, whereas the compound 17 exhibited highest percentages (76.74%) of the cancer cell proliferation inhibition.

  DOI：

  10.1111/j.1747-0285.2011.01196.x

文献信息

• Synthesis, Saccharide-Binding and Anti-cancer Cell Proliferation Properties of Arylboronic Acid Derivatives of Indoquinolines
  作者：Junxiu Meng、Shaoqing Yu、Shengbiao Wan、Sumei Ren、Tao Jiang

  DOI：10.1111/j.1747-0285.2011.01196.x

  日期：2011.11

  A facile synthesis of a series of saccharide‐binding arylboronic acid derivatives of indoloquinoline was described. The key synthetic steps were polyphosphoric acid‐mediated cyclization, chlorinative aromatization, and amidation. Mass spectrometry experiments revealed these synthetic arylboronic acid derivatives of indoquinolines could bind to biologically important carbohydrates (sialic acid, fucose, glucose, and galactose) by forming boronate di‐esters in alkaline aqueous solution. Most of the arylboronic acid derivatives of indoquinolines inhibited human breast cancer cell (MDA–231) proliferation at a concentration of 5 μm, whereas the compound 17 exhibited highest percentages (76.74%) of the cancer cell proliferation inhibition.