1-ethyl-6-fluoro-7-{4-[2-(4-fluorophenyl)-2-oxoethyl]-1-piperazinyl}-4-oxo-1,4-dihydroquinoline-3-carboxylic acid | 202925-21-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-ethyl-6-fluoro-7-{4-[2-(4-fluorophenyl)-2-oxoethyl]-1-piperazinyl}-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• 英文别名: 1-ethyl-6-fluoro-7-{4-[2-(4-fluorophenyl)-2-oxoethyl]-1-piperazinyl}-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid；1-Ethyl-6-fluoro-7-[4-[2-(4-fluorophenyl)-2-oxo-ethyl]piperazin-1-yl]-4-oxo-quinoline-3-carboxylic acid；1-ethyl-6-fluoro-7-[4-[2-(4-fluorophenyl)-2-oxoethyl]piperazin-1-yl]-4-oxoquinoline-3-carboxylic acid
• CAS: 202925-21-1
• 化学式: C₂₄H₂₃F₂N₃O₄
• 分子量: 455.461
• InChiKey: UWSYYHUZDSOUKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  81.2
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-ethyl-6-fluoro-7-{4-[2-(4-fluorophenyl)-2-oxoethyl]-1-piperazinyl}-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以72%的产率得到1-ethyl-6-fluoro-7-[4-[(2Z)-2-(4-fluorophenyl)-2-hydrazinylidene-ethyl]piperazin-1-yl]-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
• 作为产物：
  描述：

  诺氟沙星 、 2-溴-4'-氟苯乙酮 以that described for Example 4 (619 yield)的产率得到1-ethyl-6-fluoro-7-{4-[2-(4-fluorophenyl)-2-oxoethyl]-1-piperazinyl}-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  6-fluoro-1,4-dihydro-7-[4-(2-hydroxyiminoethyl)-1-piperazinyl]-4-oxoquinoline-3-carboxylic acid derivatives, their preparation and pharmaceutical compositions

  摘要：

  本发明披露了一种新型的6-氟-1,4-二氢-7-[4-(2-羟基亚胺基乙基)-1-哌嗪基]-4-氧代喹啉-3-羧酸衍生物（式I），其制备方法以及含有其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。1

  公开号：

  US20020061895A1

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 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。
• Foroumadi; Emami; Davood, Pharmaceutical Sciences, 1997, vol. 3, # 12, p. 559 - 563
  作者：Foroumadi、Emami、Davood、Moshafi、Sharifian、Tabatabaie、Farimani、Sepehri、Shafiee

  DOI：——

  日期：——
• Synthesis, Antibacterial, and Cytotoxic Evaluation of Certain 7-Substituted Norfloxacin Derivatives
  作者：Kuo-Chang Fang、Yeh-Long Chen、Jia-Yuh Sheu、Tai-Chi Wang、Cherng-Chyi Tzeng

  DOI：10.1021/jm000153x

  日期：2000.10.1

  We report herein the synthesis and biological evaluation of two series of 7-substituted norfloxacin derivatives. Most compounds tested in this study demonstrated better activity against methicillin-resistant Staphylococcus aureus than norfloxacin. Preliminary in vitro evaluation indicated that the 7-[4-(2-hydroxyiminoethyl)piperazin-1-yl] derivatives 3b-e possess distinct cytotoxicity profiles as compared with their alpha-methylene-gamma-butyrolactone counterparts, 4b,e: i.e., excellent activities against the renal cancer subpanel. Among them, 1-ethyl-6-fluoro-7-4-[2-(4-chlorophenyl)-2-hydroxyiminoethyl]-1-piperazinyl}-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid (3d) demonstrated the most significant activities against renal cancer cell lines, with log GI(50) values of -6.40 against CAK-1, -6.14 against RXF 393, and -7.54 against UO-31, compared with a mean log GI(50) value of -5.03.
• 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.