6-溴-2-(4-氯苯基)喹啉-4-羧酸 | 351327-32-7

• 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: 6-溴-2-(4-氯苯基)喹啉-4-羧酸
• 英文名称: 6-bromo-2-(4-chloro-phenyl)-quinoline-4-carboxylic acid
• 英文别名: 6-Brom-2-(4-chlor-phenyl)-chinolin-4-carbonsaeure；6-Bromo-2-(4-chlorophenyl)quinoline-4-carboxylic acid
• CAS: 351327-32-7
• 化学式: C₁₆H₉BrClNO₂
• mdl: MFCD01812642
• 分子量: 362.61
• InChiKey: DLRGQCSCQAFQBF-UHFFFAOYSA-N

物化性质

• 沸点：
  523.8±50.0 °C(Predicted)
• 密度：
  1.628±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-溴-2-(4-氯苯基)喹啉-4-羧酸 生成 6-bromo-2-(4-chloro-phenyl)-quinoline
  参考文献：
  名称：

  The Pfitzinger Reaction in the Synthesis of Quinoline Derivatives

  摘要：

  DOI：

  10.1021/jo50015a019
• 作为产物：
  描述：

  5-溴靛红 、 对氯苯乙酮 在 水 、 potassium hydroxide 作用下， 反应 24.0h， 生成 6-溴-2-(4-氯苯基)喹啉-4-羧酸
  参考文献：
  名称：

  Discovery of novel tubulin inhibitors targeting the colchicine binding site via virtual screening, structural optimization and antitumor evaluation

  摘要：

  The colchicine binding site of tubulin is a promising target for discovering novel antitumor agents which exert the antiangiogenic effect and are not susceptible to multidrug resistance. For identifying novel tubulin inhibitors, structure-based virtual screening was applied to identify hit 9 which displayed moderate tubulin polymerization inhibition and broad-spectrum in vitro antitumor activity. Structural optimization was performed, and biological assay revealed analog E27 displayed the best antitumor activity with IC50 values ranging from 7.81 μM to 10.36 μM, and improved tubulin polymerization inhibitory activity (IC50 = 16.1 μM). It significantly inhibited cancer cell migration and invasion, induced cell apoptosis and arrested the cell cycle at G2/M phase. Moreover, the apoptotic effect of E27 is related to the increased ROS level, the decrease of MMP, and the abnormal expression of apoptosis-related proteins. Taken together, these results suggested E27 was a promising lead compound for discovering novel tubulin-targeted antitumor agents.

  DOI：

  10.1016/j.bioorg.2021.105486

文献信息

• [EN] GLUCOSE TRANSPORT INHIBITORS<br/>[FR] INHIBITEURS DE TRANSPORT DU GLUCOSE
  申请人：BAYER PHARMA AG

  公开号：WO2016202898A1

  公开（公告）日：2016-12-22

  The present invention relates to chemical compounds that selectively inhibit glucose transporter 1 (GLUT1), to methods of preparing said compounds, to pharmaceutical compositions and combinations comprising said compounds, to the use of said compounds for manufacturing a pharmaceutical composition for the treatment or prophylaxis of a disease, as well as to intermediate compounds useful in the preparation of said compounds.

  本发明涉及选择性抑制葡萄糖转运蛋白1（GLUT1）的化合物，涉及制备该类化合物的方法，涉及包含该类化合物的药物组合物和药物组合物，涉及利用该类化合物制造用于治疗或预防疾病的药物组合物，以及用于制备该类化合物的中间化合物。
• The Pfitzinger Reaction in the Synthesis of Quinoline Derivatives
  作者：Ng. Ph. Buu-Hoi、R. Royer、Ng. D. Xuong、P. Jacquignon

  DOI：10.1021/jo50015a019

  日期：1953.9
• Discovery of novel tubulin inhibitors targeting the colchicine binding site via virtual screening, structural optimization and antitumor evaluation
  作者：Wei Liu、Hairui Jia、Minghao Guan、Minxuan Cui、Zhuxuan Lan、Youyou He、Zhongjie Guo、Ru Jiang、Guoqiang Dong、Shengzheng Wang

  DOI：10.1016/j.bioorg.2021.105486

  日期：2022.1

  The colchicine binding site of tubulin is a promising target for discovering novel antitumor agents which exert the antiangiogenic effect and are not susceptible to multidrug resistance. For identifying novel tubulin inhibitors, structure-based virtual screening was applied to identify hit 9 which displayed moderate tubulin polymerization inhibition and broad-spectrum in vitro antitumor activity. Structural optimization was performed, and biological assay revealed analog E27 displayed the best antitumor activity with IC50 values ranging from 7.81 μM to 10.36 μM, and improved tubulin polymerization inhibitory activity (IC50 = 16.1 μM). It significantly inhibited cancer cell migration and invasion, induced cell apoptosis and arrested the cell cycle at G2/M phase. Moreover, the apoptotic effect of E27 is related to the increased ROS level, the decrease of MMP, and the abnormal expression of apoptosis-related proteins. Taken together, these results suggested E27 was a promising lead compound for discovering novel tubulin-targeted antitumor agents.