7-chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic (ethyl carbonic) anhydride | 115391-19-0

• 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: 7-chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic (ethyl carbonic) anhydride
• CAS: 115391-19-0
• 化学式: C₁₅H₁₃ClFNO₅
• 分子量: 341.723
• InChiKey: IUYWZWGYBAJMSW-UHFFFAOYSA-N

物化性质

• 沸点：
  450.5±55.0 °C(predicted)
• 密度：
  1.406±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  74.6
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  7-chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic (ethyl carbonic) anhydride 、 4-甲氧基苄胺 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 73.0h， 以21%的产率得到7-chloro-1-ethyl-6-fluoro-N-(4-methoxybenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide
  参考文献：
  名称：

  A Small-Molecule Inhibitor of Nipah Virus Envelope Protein-Mediated Membrane Fusion

  摘要：

  Nipah virus (NiV), a highly pathogenic paramyxovirus. causes respiratory disease in pigs and severe febrile encephalitis in humans with high mortality rates. On the basis of the structural similarity of viral fusion (F) proteins within the family Paramyxoviridae, we designed and tested 18 quinolone derivatives in a NiV and measles virus (MV) envelope protein-based fusion assay beside evaluation of cytotoxicity. We found five compounds successfully inhibiting NiV envelope protein-induced cell fusion. The most active molecules (19 and 20), which also inhibit the syncytium formation induced by infectious NiV and show a low cytotoxicity in Vero cells, represent a promising lead quinolone-type compound structure. Molecular modeling indicated that compound 19 fits well into a particular protein cavity present on the NiV F protein that is important for the fusion process.

  DOI：

  10.1021/jm900411s
• 作为产物：
  描述：

  氯甲酸乙酯 、 7-氯-1-乙基-6-氟-4-氧氢喹啉-3-羧酸 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 7-chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic (ethyl carbonic) anhydride
  参考文献：
  名称：

  A Small-Molecule Inhibitor of Nipah Virus Envelope Protein-Mediated Membrane Fusion

  摘要：

  Nipah virus (NiV), a highly pathogenic paramyxovirus. causes respiratory disease in pigs and severe febrile encephalitis in humans with high mortality rates. On the basis of the structural similarity of viral fusion (F) proteins within the family Paramyxoviridae, we designed and tested 18 quinolone derivatives in a NiV and measles virus (MV) envelope protein-based fusion assay beside evaluation of cytotoxicity. We found five compounds successfully inhibiting NiV envelope protein-induced cell fusion. The most active molecules (19 and 20), which also inhibit the syncytium formation induced by infectious NiV and show a low cytotoxicity in Vero cells, represent a promising lead quinolone-type compound structure. Molecular modeling indicated that compound 19 fits well into a particular protein cavity present on the NiV F protein that is important for the fusion process.

  DOI：

  10.1021/jm900411s