1-cyclopropyl-6-fluoro-7-(4-(2-methoxy-2-oxoethyl)piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-cyclopropyl-6-fluoro-7-(4-(2-methoxy-2-oxoethyl)piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• 英文别名: 1-Cyclopropyl-6-fluoro-7-[4-(2-methoxy-2-oxoethyl)piperazin-1-yl]-4-oxoquinoline-3-carboxylic acid
• 化学式: C₂₀H₂₂FN₃O₅
• 分子量: 403.41
• InChiKey: YNZVLEOKKXRBDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  90.4
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-cyclopropyl-6-fluoro-7-(4-(2-methoxy-2-oxoethyl)piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 在 硫酸 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 3.0h， 以84%的产率得到7-(4-(carboxymethyl)piperazin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and antibacterial activity of catecholate–ciprofloxacin conjugates

  摘要：

  The development of an efficient route to obtain artificial siderophore antibiotic conjugates active against Gram-negative bacteria is crucial. Herein, a practical access to triscatecholate enterobactin analogues linked to the ciprofloxacin along with their antibacterial evaluation are described. Two series of conjugates were obtained with and without a piperazine linker which is known to improve the pharmacokinetics profile of a drug. A monocatecholate-ciprofloxacin conjugate was also synthesized and evaluated. The antibacterial activities against Pseudomonas aeruginosa for some conjugates are related to the iron concentration in the culture medium and seem to depend on the bacterial iron uptake systems. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.05.067
• 作为产物：
  描述：

  环丙沙星 、 溴乙酸甲酯 在 三乙胺 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-cyclopropyl-6-fluoro-7-(4-(2-methoxy-2-oxoethyl)piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  Anionic fluoroquinolones as antibacterials against biofilm-producing Pseudomonas aeruginosa

  摘要：

  Pseudomonas aeruginosa is a common biofilm-forming bacterial pathogen implicated in diseases of the lungs. The extracellular polymeric substances (EPS) of respiratory Pseudomonas biofilms are largely comprised of anionic molecules such as rhamnolipids and alginate that promote a mucoid phenotype. In this Letter, we examine the ability of negatively-charged fluoroquinolones to transverse the EPS and inhibit the growth of mucoid P. aeruginosa. Anionic fluoroquinolones were further compared with standard antibiotics via a novel microdiffusion assay to evaluate drug penetration through pseudomonal alginate and respiratory mucus from a patient with cystic fibrosis. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.01.012

文献信息

• Chinoloncarbonsäure enthaltende bakterizide Mittel
  申请人：BAYER AG

  公开号：EP0118854A1

  公开（公告）日：1984-09-19

  Die Erfindung betrifft die Verwendung von Chinoloncarbonsäuren der Formel (I) in der R1, R2, R3, R", R5, R6 und X die in der Beschreibung angegebene Bedeutung haben, als Bakterizide.

  本发明涉及式（I）喹啉羧酸作为杀菌剂的用途。 其中 R1、R2、R3、R"、R5、R6 和 X 具有说明中给出的含义，可用作杀菌剂。
• Synthesis and antibacterial activity of catecholate–ciprofloxacin conjugates
  作者：Sylvain Fardeau、Alexandra Dassonville-Klimpt、Nicolas Audic、André Sasaki、Marine Pillon、Emmanuel Baudrin、Catherine Mullié、Pascal Sonnet

  DOI：10.1016/j.bmc.2014.05.067

  日期：2014.8

  The development of an efficient route to obtain artificial siderophore antibiotic conjugates active against Gram-negative bacteria is crucial. Herein, a practical access to triscatecholate enterobactin analogues linked to the ciprofloxacin along with their antibacterial evaluation are described. Two series of conjugates were obtained with and without a piperazine linker which is known to improve the pharmacokinetics profile of a drug. A monocatecholate-ciprofloxacin conjugate was also synthesized and evaluated. The antibacterial activities against Pseudomonas aeruginosa for some conjugates are related to the iron concentration in the culture medium and seem to depend on the bacterial iron uptake systems. (C) 2014 Elsevier Ltd. All rights reserved.
• US4563448A
  申请人：——

  公开号：US4563448A

  公开（公告）日：1986-01-07
• US4559342A
  申请人：——

  公开号：US4559342A

  公开（公告）日：1985-12-17
• Anionic fluoroquinolones as antibacterials against biofilm-producing Pseudomonas aeruginosa
  作者：Timothy E. Long、Lexie C. Keding、Demetria D. Lewis、Michael I. Anstead、T. Ryan Withers、Hongwei D. Yu

  DOI：10.1016/j.bmcl.2016.01.012

  日期：2016.2

  Pseudomonas aeruginosa is a common biofilm-forming bacterial pathogen implicated in diseases of the lungs. The extracellular polymeric substances (EPS) of respiratory Pseudomonas biofilms are largely comprised of anionic molecules such as rhamnolipids and alginate that promote a mucoid phenotype. In this Letter, we examine the ability of negatively-charged fluoroquinolones to transverse the EPS and inhibit the growth of mucoid P. aeruginosa. Anionic fluoroquinolones were further compared with standard antibiotics via a novel microdiffusion assay to evaluate drug penetration through pseudomonal alginate and respiratory mucus from a patient with cystic fibrosis. (C) 2016 Elsevier Ltd. All rights reserved.