7-(3-benzylideneaminomethyl-4-difluoromethoxyimino-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid | 1356857-74-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 7-(3-benzylideneaminomethyl-4-difluoromethoxyimino-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
• CAS: 1356857-74-3
• 化学式: C₂₅H₂₂F₃N₅O₄
• 分子量: 513.476
• InChiKey: CUPBXUYXNKCGMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  37.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  109.38
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  甲烷磺酸 、 7-(3-benzylideneaminomethyl-4-difluoromethoxyimino-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid 以 乙醇 、 水 为溶剂， 反应 16.0h， 以65.4%的产率得到7-(3-aminomethyl-4-difluoromethoxyimino-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid methanesulfonate
  参考文献：
  名称：

  Synthesis and antibacterial activity of naphthyridone derivatives containing mono/difluoro-methyloxime pyrrolidine scaffolds

  摘要：

  A series of novel naphthyridone derivatives containing mono/difluoro-methyloxime pyrrolidine scaffolds were designed and synthesized. These derivatives were initially evaluated for their in vitro antibacterial activity and compounds 13a1, b1 were chosen for further evaluation their in vivo activity against systemic infections in mice. The results indicate that all of the target compounds have considerable in vitro antibacterial activity. In the in vivo experiments, 13b1 was found to be more effective than the parent drug gemifloxacin against the tested five strains, and especially its activity (ED50:21.27 mg/kg) is 5.2-6.1 times more potent than gemifloxacin and ciprofloxacin against clinically important Gram-negative pathogen Pseudomonas aeruginosa. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.10.048
• 作为产物：
  描述：

  3-aminomethyl-4-(difluoromethoxyimino)pyrrolidine dimethanesulfonate 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 14.0h， 生成 7-(3-benzylideneaminomethyl-4-difluoromethoxyimino-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and antibacterial activity of naphthyridone derivatives containing mono/difluoro-methyloxime pyrrolidine scaffolds

  摘要：

  A series of novel naphthyridone derivatives containing mono/difluoro-methyloxime pyrrolidine scaffolds were designed and synthesized. These derivatives were initially evaluated for their in vitro antibacterial activity and compounds 13a1, b1 were chosen for further evaluation their in vivo activity against systemic infections in mice. The results indicate that all of the target compounds have considerable in vitro antibacterial activity. In the in vivo experiments, 13b1 was found to be more effective than the parent drug gemifloxacin against the tested five strains, and especially its activity (ED50:21.27 mg/kg) is 5.2-6.1 times more potent than gemifloxacin and ciprofloxacin against clinically important Gram-negative pathogen Pseudomonas aeruginosa. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.10.048