N-(3-morpholinopropyl) 6-fluoro-7-methoxy-4-oxo-2-(3-phenoxyphenyl)-1,4-dihydroquinoline-3-carboxamide | 1373766-82-5

• 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: N-(3-morpholinopropyl) 6-fluoro-7-methoxy-4-oxo-2-(3-phenoxyphenyl)-1,4-dihydroquinoline-3-carboxamide
• 英文别名: 6-fluoro-7-methoxy-N-(3-morpholinopropyl)-4-oxo-2-(3-phenoxyphenyl)-1H-quinoline-3-carboxamide；6-fluoro-7-methoxy-N-(3-morpholin-4-ylpropyl)-4-oxo-2-(3-phenoxyphenyl)-1H-quinoline-3-carboxamide
• CAS: 1373766-82-5
• 化学式: C₃₀H₃₀FN₃O₅
• 分子量: 531.584
• InChiKey: SKDVIFQPTXGYRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  39
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  89.1
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  在 水 、 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 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 43.5h， 生成 N-(3-morpholinopropyl) 6-fluoro-7-methoxy-4-oxo-2-(3-phenoxyphenyl)-1,4-dihydroquinoline-3-carboxamide
  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