(RS)-1-ethyl-6,8-difluoro-1,4-dihydro-7-[3-methyl-4-((5-nitrofuran-2-yl)methyl)piperazin-1-yl]-4-oxo-quinoline-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: (RS)-1-ethyl-6,8-difluoro-1,4-dihydro-7-[3-methyl-4-((5-nitrofuran-2-yl)methyl)piperazin-1-yl]-4-oxo-quinoline-3-carboxylic acid
• 英文别名: 1-Ethyl-6,8-difluoro-7-[3-methyl-4-[(5-nitrofuran-2-yl)methyl]piperazin-1-yl]-4-oxoquinoline-3-carboxylic acid；1-ethyl-6,8-difluoro-7-[3-methyl-4-[(5-nitrofuran-2-yl)methyl]piperazin-1-yl]-4-oxoquinoline-3-carboxylic acid
• 化学式: C₂₂H₂₂F₂N₄O₆
• 分子量: 476.437
• InChiKey: HSSBYGCSVOTADM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  122.06
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  5-硝基糠醇 在 三溴化磷 、 碳酸氢钠 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 121.0h， 生成 (RS)-1-ethyl-6,8-difluoro-1,4-dihydro-7-[3-methyl-4-((5-nitrofuran-2-yl)methyl)piperazin-1-yl]-4-oxo-quinoline-3-carboxylic acid
  参考文献：
  名称：

  7-Piperazinylquinolones with methylene-bridged nitrofuran scaffold as new antibacterial agents

  摘要：

  Quinolone class of antibacterial agents has considerable attention to find new useful antibacterial agents. Therefore, a series of N-substituted piperazinylquinolones bearing (5-nitrofuran-2-yl)methyl moiety were synthesized and evaluated against a variety of bacteria. The methylene-bridged nitrofuran functionality has been recently used in oxazolidinone class of antibacterial agents containing piperazinyl moiety by introducing ranbezolid as a 5-nitrofuran analog of eperzolid. The results of antibacterial evaluation revealed that the influence of (5-nitrofuran-2-yl) attachment to the 7-piperazinylquinolones against different bacterial species depends on the type of substituents at the N-1 and C-8 positions. Better results were obtained with ethyl at N-1 and CF at C-8 in the term of activity against Bacillus subtilis and E. coli. While, the optimum activity against Staphylococcus aureus, Pseudomonas aeruginosa, and Klebsiella pneumonia was entailed by a molecule possessing cyclopropyl at N-1 and CH at C-8.

  DOI：

  10.1007/s00044-013-0581-9

文献信息

• 7-Piperazinylquinolones with methylene-bridged nitrofuran scaffold as new antibacterial agents
  作者：Saeed Emami、Nima Shahrokhirad、Alireza Foroumadi、Mohammad Ali Faramarzi、Nasrin Samadi、Narges Soltani-Ghofrani

  DOI：10.1007/s00044-013-0581-9

  日期：2013.12

  Quinolone class of antibacterial agents has considerable attention to find new useful antibacterial agents. Therefore, a series of N-substituted piperazinylquinolones bearing (5-nitrofuran-2-yl)methyl moiety were synthesized and evaluated against a variety of bacteria. The methylene-bridged nitrofuran functionality has been recently used in oxazolidinone class of antibacterial agents containing piperazinyl moiety by introducing ranbezolid as a 5-nitrofuran analog of eperzolid. The results of antibacterial evaluation revealed that the influence of (5-nitrofuran-2-yl) attachment to the 7-piperazinylquinolones against different bacterial species depends on the type of substituents at the N-1 and C-8 positions. Better results were obtained with ethyl at N-1 and CF at C-8 in the term of activity against Bacillus subtilis and E. coli. While, the optimum activity against Staphylococcus aureus, Pseudomonas aeruginosa, and Klebsiella pneumonia was entailed by a molecule possessing cyclopropyl at N-1 and CH at C-8.