6-Fluoro-7-[4-[2-(4-fluorophenyl)-2-oxo-ethyl]piperazin-1-yl]-1-(4-nitrophenyl)-4-oxo-quinoline-3-carboxylic acid | 353794-11-3

• 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: 6-Fluoro-7-[4-[2-(4-fluorophenyl)-2-oxo-ethyl]piperazin-1-yl]-1-(4-nitrophenyl)-4-oxo-quinoline-3-carboxylic acid
• 英文别名: 6-fluoro-7-[4-[2-(4-fluorophenyl)-2-oxoethyl]piperazin-1-yl]-1-(4-nitrophenyl)-4-oxoquinoline-3-carboxylic acid
• CAS: 353794-11-3
• 化学式: C₂₈H₂₂F₂N₄O₆
• 分子量: 548.503
• InChiKey: WAOFNVCMBRFNOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  40
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  6-Fluoro-7-[4-[2-(4-fluorophenyl)-2-oxo-ethyl]piperazin-1-yl]-1-(4-nitrophenyl)-4-oxo-quinoline-3-carboxylic acid 在 盐酸羟胺 、 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以85%的产率得到6-fluoro-7-{4-[2-(4-fluorophenyl)-2-hydroxyiminoethyl]-1-piperazinyl}-1-(4-nitrophenyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid
  参考文献：
  名称：

  Synthesis and Antibacterial Evaluation of Certain Quinolone Derivatives

  摘要：

  A number of 7-substituted quinolone derivatives were synthesized and evaluated for antibacterial and cytotoxic activities. Preliminary results indicated that most compounds tested in this study demonstrated better activity against methicillin-resistant Staphylococcus aureus than norfloxacin. Among them, 1-(4-amino-2-fluorophenyl)-6-fluoro-1,4-dihydro-7-{4-[2-(4-methoxyphenyl)-2-hydroxyiminoethyl]-1-piperazinyl}-4-oxo-3-quinolinecarboxylic acid (11d) and its ketone precursor 10d exhibited significant activities against Klebsiella pneumoniae, methicillin-resistant S. aureus, erythromycin- and ampicillin-resistant Streptococcus pneumoniae, and vancomycin-resistant Enterococcus faecalis. Due to strong cytotoxicities of lid (a mean log GI(50) of -5.40), compound 10d, with good antibacterial activities and low cytotoxicities (a mean log GI(50) of -4.67), is a more potential drug candidate.

  DOI：

  10.1021/jm0100335
• 作为产物：
  描述：

  6,7-Difluoro-1-(4-nitro-phenyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester 在 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 24.0h， 生成 6-Fluoro-7-[4-[2-(4-fluorophenyl)-2-oxo-ethyl]piperazin-1-yl]-1-(4-nitrophenyl)-4-oxo-quinoline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and Antibacterial Evaluation of Certain Quinolone Derivatives

  摘要：

  A number of 7-substituted quinolone derivatives were synthesized and evaluated for antibacterial and cytotoxic activities. Preliminary results indicated that most compounds tested in this study demonstrated better activity against methicillin-resistant Staphylococcus aureus than norfloxacin. Among them, 1-(4-amino-2-fluorophenyl)-6-fluoro-1,4-dihydro-7-{4-[2-(4-methoxyphenyl)-2-hydroxyiminoethyl]-1-piperazinyl}-4-oxo-3-quinolinecarboxylic acid (11d) and its ketone precursor 10d exhibited significant activities against Klebsiella pneumoniae, methicillin-resistant S. aureus, erythromycin- and ampicillin-resistant Streptococcus pneumoniae, and vancomycin-resistant Enterococcus faecalis. Due to strong cytotoxicities of lid (a mean log GI(50) of -5.40), compound 10d, with good antibacterial activities and low cytotoxicities (a mean log GI(50) of -4.67), is a more potential drug candidate.

  DOI：

  10.1021/jm0100335