ethyl 2-bromo-4-chloro-6-fluoro-7-methoxyquinoline-3-carboxylate | 1373767-68-0

• 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: ethyl 2-bromo-4-chloro-6-fluoro-7-methoxyquinoline-3-carboxylate
• CAS: 1373767-68-0
• 化学式: C₁₃H₁₀BrClFNO₃
• 分子量: 362.583
• InChiKey: GZCYWJCHONQYFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  48.42
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-bromo-4-chloro-6-fluoro-7-methoxyquinoline-3-carboxylate 在 四(三苯基膦)钯 、 水 、 caesium carbonate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 溶剂黄146 、 N,N-二异丙基乙胺 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 46.5h， 生成 2-(pyrrolidin-1-yl)ethyl 6-fluoro-7-methoxy-4-oxo-2-(3-phenoxyphenyl)-1,4-dihydroquinoline-3-carboxylate
  参考文献：
  名称：

  Lead Optimization of 3-Carboxyl-4(1H)-Quinolones to Deliver Orally Bioavailable Antimalarials

  摘要：

  Malaria is a protozoal parasitic disease that is widespread in tropical and subtropical regions of Africa, Asia, and the Americas and causes more than 800,000 deaths per year. The continuing emergence of multidrug-resistant Plasmodium falciparum drives the ongoing need for the development of new and effective antimalarial drugs. Our previous work has explored the preliminary structural optimization of 4(1H)-quinolone ester derivatives, a new series of antimalarials related to the endochins. Herein, we report the lead optimization of 4(1H)-quinolones with a focus on improving both antimalarial potency and bioavailability. These studies led to the development of orally efficacious antimalarials including quinolone analogue 20g, a promising candidate for further optimization.

  DOI：

  10.1021/jm201642z
• 作为产物：
  描述：

  4-氟-3-甲氧基苯胺 在 间氯过氧苯甲酸 、 三氯氧磷 、 三溴氧磷 作用下， 以 1,4-二氧六环 、 二苯醚 、 乙醇 、 氯仿 为溶剂， 反应 10.0h， 生成 ethyl 2-bromo-4-chloro-6-fluoro-7-methoxyquinoline-3-carboxylate
  参考文献：
  名称：

  Lead Optimization of 3-Carboxyl-4(1H)-Quinolones to Deliver Orally Bioavailable Antimalarials

  摘要：

  Malaria is a protozoal parasitic disease that is widespread in tropical and subtropical regions of Africa, Asia, and the Americas and causes more than 800,000 deaths per year. The continuing emergence of multidrug-resistant Plasmodium falciparum drives the ongoing need for the development of new and effective antimalarial drugs. Our previous work has explored the preliminary structural optimization of 4(1H)-quinolone ester derivatives, a new series of antimalarials related to the endochins. Herein, we report the lead optimization of 4(1H)-quinolones with a focus on improving both antimalarial potency and bioavailability. These studies led to the development of orally efficacious antimalarials including quinolone analogue 20g, a promising candidate for further optimization.

  DOI：

  10.1021/jm201642z