10,11-dihydro-11-oxo-5H-indolo[3,2-b]quinoline-9-carboxylic acid | 1346173-72-5

• 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
• 英文名称: 10,11-dihydro-11-oxo-5H-indolo[3,2-b]quinoline-9-carboxylic acid
• 英文别名: 11-Oxo-5,10-dihydroindolo[3,2-b]quinoline-9-carboxylic acid
• CAS: 1346173-72-5
• 化学式: C₁₆H₁₀N₂O₃
• 分子量: 278.267
• InChiKey: SHUZNNAPMFUWFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 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：
  82.2
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  10,11-dihydro-11-oxo-5H-indolo[3,2-b]quinoline-9-carboxylic acid 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氯氧磷 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 46.0h， 生成 3-(11-chloro-10H-indolo[3,2-b]quinoline-9-carboxamido)phenylboronic 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
• 作为产物：
  描述：

  2-(2-溴乙酰氨基)苯甲酸甲酯 在 水 、 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 10,11-dihydro-11-oxo-5H-indolo[3,2-b]quinoline-9-carboxylic acid
  参考文献：
  名称：

  新型降血脂素类似物的合成及其对肿瘤细胞的细胞毒性

  摘要：

  设计并合成了六种新颖的生物活性天然吲哚并[3,2- b ]喹啉生物碱苷芥子油苷，采用多磷酸介导的环化作用和两种不同的酰胺化策略，将四-O-乙酰-β - d-葡糖胺引入四环羧酸酸。

  DOI：

  10.1002/jhet.2381

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.
• Synthesis of Novel Jusbetonin Analogues and Their Cytotoxicity against Tumor Cell
  作者：Shixu Liu、Junxiu Meng、Wei Zhang、Shengbiao Wan、Tao Jiang

  DOI：10.1002/jhet.2381

  日期：2016.7

  Six novel analogues of bioactive natural indolo[3,2‐b]quinoline alkaloid glycoside jusbetonin were designed and synthesized, employing polyphosphoric acid mediated cyclization and two different amidation strategies on introduction of tetra‐O‐acetyl‐β‐d‐glucosamine to tetracyclic carboxylic acids.

  设计并合成了六种新颖的生物活性天然吲哚并[3,2- b ]喹啉生物碱苷芥子油苷，采用多磷酸介导的环化作用和两种不同的酰胺化策略，将四-O-乙酰-β - d-葡糖胺引入四环羧酸酸。