ethyl 7-chloro-6-fluoro-1-(4-methoxyphenyl)-4-oxo-1,8-naphthyridine-3-carboxylate | 100491-40-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: ethyl 7-chloro-6-fluoro-1-(4-methoxyphenyl)-4-oxo-1,8-naphthyridine-3-carboxylate
• CAS: 100491-40-5
• 化学式: C₁₈H₁₄ClFN₂O₄
• 分子量: 376.772
• InChiKey: MPBSFEFFCDTCTK-UHFFFAOYSA-N

物化性质

• 熔点：
  196-198 °C
• 沸点：
  544.4±50.0 °C(Predicted)
• 密度：
  1.412±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  70.42
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl 7-chloro-6-fluoro-1-(4-methoxyphenyl)-4-oxo-1,8-naphthyridine-3-carboxylate 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到7-Chloro-6-fluoro-1-(4-hydroxy-phenyl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid
  参考文献：
  名称：

  A Prodrug Approach toward the Development of Water Soluble Fluoroquinolones and Structure−Activity Relationships of Quinoline-3-carboxylic Acids

  摘要：

  A fluoroquinolone prodrug, PA2808, was prepared and shown to convert to the highly active parent drug PA2789. In vitro and in vivo activation of PA2808 by alkaline phosphatase was demonstrated using disk diffusion and rat lung infection models. The water solubility of PA2808 showed a marked increase compared to PA2789 over a pH range suitable for aerosol drug delivery. A total of 48 analogues based on PA2789 were prepared and screened against a panel of Gram-positive and Gram-negative pathogens. Incorporating a cyclopropane-fused pyrrolidine (amine g) at C-7 resulted in some of the most active analogues.

  DOI：

  10.1021/jm0497895
• 作为产物：
  描述：

  ethyl 3-(2,6-dichloro-5-fluoropyridin-3-yl)-3-oxopropanoate 在 乙酸酐 、 potassium carbonate 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 ethyl 7-chloro-6-fluoro-1-(4-methoxyphenyl)-4-oxo-1,8-naphthyridine-3-carboxylate
  参考文献：
  名称：

  A Prodrug Approach toward the Development of Water Soluble Fluoroquinolones and Structure−Activity Relationships of Quinoline-3-carboxylic Acids

  摘要：

  A fluoroquinolone prodrug, PA2808, was prepared and shown to convert to the highly active parent drug PA2789. In vitro and in vivo activation of PA2808 by alkaline phosphatase was demonstrated using disk diffusion and rat lung infection models. The water solubility of PA2808 showed a marked increase compared to PA2789 over a pH range suitable for aerosol drug delivery. A total of 48 analogues based on PA2789 were prepared and screened against a panel of Gram-positive and Gram-negative pathogens. Incorporating a cyclopropane-fused pyrrolidine (amine g) at C-7 resulted in some of the most active analogues.

  DOI：

  10.1021/jm0497895

文献信息

• NARITA, XIROKADZU;KONISI, JOSINORI;NITTA, DZYUN;NAGAKI, XIDEHESI;KITAYAMA+
  作者：NARITA, XIROKADZU、KONISI, JOSINORI、NITTA, DZYUN、NAGAKI, XIDEHESI、KITAYAMA+

  DOI：——

  日期：——