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

• 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-cyclopropyl-7-(4-(2,3-dihydroxybenzoyl)piperazin-1-yl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• 英文别名: 1-Cyclopropyl-7-[4-(2,3-dihydroxybenzoyl)piperazin-1-yl]-6-fluoro-4-oxoquinoline-3-carboxylic acid；1-cyclopropyl-7-[4-(2,3-dihydroxybenzoyl)piperazin-1-yl]-6-fluoro-4-oxoquinoline-3-carboxylic acid
• 化学式: C₂₄H₂₂FN₃O₆
• 分子量: 467.454
• InChiKey: VGOIZJNXCMMPBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  122
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  苯甲酸,二羟基- 在 三聚氟氰 、 硫酸 、 10 wt% Pd(OH)2 on carbon 、 氢气 、 potassium carbonate 、 三乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 146.0h， 生成 1-cyclopropyl-7-(4-(2,3-dihydroxybenzoyl)piperazin-1-yl)-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

文献信息

• 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.