7-[(carboxymethyl)amino]-1-cyclopropyl-6-fluoro-8-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid | 914478-39-0

• 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: 7-[(carboxymethyl)amino]-1-cyclopropyl-6-fluoro-8-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• 英文别名: 7-(Carboxymethylamino)-1-cyclopropyl-6-fluoro-8-nitro-4-oxoquinoline-3-carboxylic acid
• CAS: 914478-39-0
• 化学式: C₁₅H₁₂FN₃O₇
• 分子量: 365.275
• InChiKey: CKMLMQVHVCTBIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  153
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  7-[(carboxymethyl)amino]-1-cyclopropyl-6-fluoro-8-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 在 sodium dithionite 、 potassium carbonate 、 三乙胺 作用下， 以 氯仿 、 水 为溶剂， 反应 48.42h， 生成 4-acetyl-10-cyclopropyl-5-fluoro-2,7-dioxo-1,2,3,4,7,10-hexahydropyrido[2,3-f]quinoxaline-8-carboxylic acid
  参考文献：
  名称：

  Synthesis and antibacterial properties of new N₄-acetylated hexahydro-2,7-dioxopyrido[2,3-f]quinoxaline-8-carboxylic acids

  摘要：

  Direct interaction between 7-chloro-1-cyclopropyl-6-fluoro-8-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid and primary alpha-amino acids (exemplified by glycine, alanine, and l-valine) in aqueous ethanolic NaHCO3 at 70-80 degrees C for 24-72 h produced the respective N-(4-oxoquinolin-7-yl)-alpha-amino acids (6a-c). The latter derivatives underwent reductive lactamization upon treatment with Na2S2O4 in aqueous ethanol to afford moderate yields of the corresponding pyrido[2,3-f]quinoxaline-8-carboxylic acids (8a-c). Acetylation of 8a-c using acetyl chloride afforded N-4-acetylated hexahydro-2,7-dioxopyrido[2,3-f] quinoxaline-8-carboxylic acids (9a-c). The structures, assigned to these new heterocyclic products, are supported by analytical and spectral data. The synthesized compounds (6a-c/9a-c) showed appreciable antibacterial activity as compared with ciprofloxacin.

  DOI：

  10.3109/14756366.2010.543421
• 作为产物：
  描述：

  7-氯-1-环丙基-6-氟-8-硝基-4-氧代-1,4-二氢喹啉-3-羧酸 、 聚甘氨酸 在 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 反应 48.0h， 以82%的产率得到7-[(carboxymethyl)amino]-1-cyclopropyl-6-fluoro-8-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and antibacterial properties of new N₄-acetylated hexahydro-2,7-dioxopyrido[2,3-f]quinoxaline-8-carboxylic acids

  摘要：

  Direct interaction between 7-chloro-1-cyclopropyl-6-fluoro-8-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid and primary alpha-amino acids (exemplified by glycine, alanine, and l-valine) in aqueous ethanolic NaHCO3 at 70-80 degrees C for 24-72 h produced the respective N-(4-oxoquinolin-7-yl)-alpha-amino acids (6a-c). The latter derivatives underwent reductive lactamization upon treatment with Na2S2O4 in aqueous ethanol to afford moderate yields of the corresponding pyrido[2,3-f]quinoxaline-8-carboxylic acids (8a-c). Acetylation of 8a-c using acetyl chloride afforded N-4-acetylated hexahydro-2,7-dioxopyrido[2,3-f] quinoxaline-8-carboxylic acids (9a-c). The structures, assigned to these new heterocyclic products, are supported by analytical and spectral data. The synthesized compounds (6a-c/9a-c) showed appreciable antibacterial activity as compared with ciprofloxacin.

  DOI：

  10.3109/14756366.2010.543421

文献信息

• Quinoline and pyridoquinoxaline derivatives as antibacterial agents
  申请人：University of Jordan

  公开号：EP1721898B1

  公开（公告）日：2011-03-16