5,6,7,8-Tetrafluoro-1-(4-fluoro-phenyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid | 107564-04-5

• 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: 5,6,7,8-Tetrafluoro-1-(4-fluoro-phenyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
• 英文别名: 5,6,7,8-tetrafluoro-1-(4-fluorophenyl)-4-oxoquinoline-3-carboxylic acid
• CAS: 107564-04-5
• 化学式: C₁₆H₆F₅NO₃
• 分子量: 355.221
• InChiKey: UUYDGLMAKLSZFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59.3
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-甲基哌嗪 、 5,6,7,8-Tetrafluoro-1-(4-fluoro-phenyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 以 various solvent(s) 为溶剂， 以85%的产率得到5,6,8-Trifluoro-1-(4-fluoro-phenyl)-7-(4-methyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis of novel 5-fluoro analogs of norfloxacin and ciprofloxacin

  摘要：

  A series of polyfluoro-3-quinolonecarboxylic acids have been synthesized and their in vitro antibacterial activity evaluated. The desired 7-(substituted amino) derivatives were prepared from the 5,6,7,8-tetrafluoroquinolone acids. Conversely, amine displacement occurred primarily at the 5-position when the ester was used. Structure-activity studies indicated that the antibacterial activity was greatest when the N-1 substituent was cyclopropyl and the 7-substituent was 4-methyl-1-piperazinyl. All 5-(substituted amino) derivatives showed poor in vitro activity.

  DOI：

  10.1021/jm00126a028
• 作为产物：
  描述：

  ethyl 2-ethoxymethylene-3-oxo-3-pentafluorophenylpropionate 在 硫酸 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 5,6,7,8-Tetrafluoro-1-(4-fluoro-phenyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis of novel 5-fluoro analogs of norfloxacin and ciprofloxacin

  摘要：

  A series of polyfluoro-3-quinolonecarboxylic acids have been synthesized and their in vitro antibacterial activity evaluated. The desired 7-(substituted amino) derivatives were prepared from the 5,6,7,8-tetrafluoroquinolone acids. Conversely, amine displacement occurred primarily at the 5-position when the ester was used. Structure-activity studies indicated that the antibacterial activity was greatest when the N-1 substituent was cyclopropyl and the 7-substituent was 4-methyl-1-piperazinyl. All 5-(substituted amino) derivatives showed poor in vitro activity.

  DOI：

  10.1021/jm00126a028