1-(4-amino-2-fluorophenyl)-6-fluoro-7-{4-[2-(4-methoxy-phenyl)-2-oxoethyl]-1-piperazinyl}-4-oxo-1,4-dihydroquinoline-3-carboxylic acid | 353794-14-6

• 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: 1-(4-amino-2-fluorophenyl)-6-fluoro-7-{4-[2-(4-methoxy-phenyl)-2-oxoethyl]-1-piperazinyl}-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• 英文别名: 7-[4-(4-Methoxyphenacyl)piperazino]-1-(2-fluoro-4-aminophenyl)-4-oxo-6-fluoro-1,4-dihydroquinoline-3-carboxylic acid；1-(4-amino-2-fluorophenyl)-6-fluoro-7-[4-[2-(4-methoxyphenyl)-2-oxoethyl]piperazin-1-yl]-4-oxoquinoline-3-carboxylic acid
• CAS: 353794-14-6
• 化学式: C₂₉H₂₆F₂N₄O₅
• 分子量: 548.546
• InChiKey: SGEXKBUPUPMDHN-UHFFFAOYSA-N

物化性质

• 沸点：
  797.3±60.0 °C(Predicted)
• 密度：
  1.419±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  40
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1-(4-amino-2-fluorophenyl)-6-fluoro-7-{4-[2-(4-methoxy-phenyl)-2-oxoethyl]-1-piperazinyl}-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 在 盐酸羟胺 、 碳酸氢钠 作用下， 以 乙醇 为溶剂， 以81%的产率得到1-(4-amino-2-fluorophenyl)-6-fluoro-7-{4-[2-(4-methoxyphenyl)-2-hydroxyiminoethyl]-1-piperazinyl}-4-oxo-1,4-dihyro-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：

  3,4-二氟硝基苯 在 palladium on activated charcoal 盐酸 、 氢气 、 碳酸氢钠 、 potassium carbonate 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 54.0h， 生成 1-(4-amino-2-fluorophenyl)-6-fluoro-7-{4-[2-(4-methoxy-phenyl)-2-oxoethyl]-1-piperazinyl}-4-oxo-1,4-dihydroquinoline-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

文献信息

• 6-fluoro-1,4-dihydro-7-[4-(2-hydroxyiminoethyl)-1-piperazinyl]-4-oxoquinoline-3-carboxylic acid derivatives, their preparation and pharmaceutical compositions
  申请人：Pharmaceutical Industry Technology

  公开号：US20020061895A1

  公开（公告）日：2002-05-23

  The present invention discloses a novel 6-fluoro-1,4-dihydro-7-[4-(2-hydroxyiminoethyl)-1-piperazinyl]-4-oxoquinoline-3-carboxylic acid derivatives (formula I), with a process for their preparation, and with pharmaceutical compositions containing them as the active ingredient for the treatment of bacterial infections and/or renal cancer diseases. 1

  本发明揭示了一种新颖的6-氟-1,4-二氢-7-[4-(2-羟基亚胺基乙基)-1-哌嗪基]-4-氧喹啉-3-羧酸衍生物（式I），以及它们的制备方法和含有它们作为活性成分的药物组合物，用于治疗细菌感染和/或肾癌疾病。
• 6-fluoro-1,4-dihydro-7-[4-(2-hydroxyiminoethyl)-1-piperazinyl]-4-oxoquinoline-3-carboxylic acid derivatives, their preparation and pharmaceutical compositions
  申请人：Pharmaceutical Industry Technology and Development Center

  公开号：US06492373B2

  公开（公告）日：2002-12-10

  The present invention discloses a novel 6-fluoro-1,4-dihydro-7-[4-(2-hydroxyiminoethyl)-1-piperazinyl]-4-oxoquinoline-3-carboxylic acid derivatives (formula I), with a process for their preparation, and with pharmaceutical compositions containing them as the active ingredient for the treatment of bacterial infections and/or renal cancer diseases.

  本发明揭示了一种新型的6-氟-1,4-二氢-7-[4-(2-羟基亚胺乙基)-1-哌嗪基]-4-氧代喹啉-3-羧酸衍生物（式I），其制备过程以及含有它们作为活性成分的药物组合物，用于治疗细菌感染和/或肾癌疾病。
• US6492373B2
  申请人：——

  公开号：US6492373B2

  公开（公告）日：2002-12-10
• Synthesis and Antibacterial Evaluation of Certain Quinolone Derivatives
  作者：Yeh-Long Chen、Kuo-Chang Fang、Jia-Yuh Sheu、Shu-Lin Hsu、Cherng-Chyi Tzeng

  DOI：10.1021/jm0100335

  日期：2001.7.1

  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.