3-(11-chloro-10H-indolo[3,2-b]quinoline-9-carboxamido)phenylboronic acid | 1346173-76-9

• 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-(11-chloro-10H-indolo[3,2-b]quinoline-9-carboxamido)phenylboronic acid
• 英文别名: [3-[(11-chloro-10H-indolo[3,2-b]quinoline-9-carbonyl)amino]phenyl]boronic acid
• CAS: 1346173-76-9
• 化学式: C₂₂H₁₅BClN₃O₃
• 分子量: 415.643
• InChiKey: GGSIPYNFNMMVPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  98.2
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(11-chloro-10H-indolo[3,2-b]quinoline-9-carboxamido)phenylboronic acid 在 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 23.0h， 以65%的产率得到3-(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：

  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

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.