4-acetyl-10-cyclopropyl-5-fluoro-2,7-dioxo-1,2,3,4,7,10-hexahydropyrido[2,3-f]quinoxaline-8-carboxylic acid | 1338095-76-3

• 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: 4-acetyl-10-cyclopropyl-5-fluoro-2,7-dioxo-1,2,3,4,7,10-hexahydropyrido[2,3-f]quinoxaline-8-carboxylic acid
• 英文别名: 4-Acetyl-10-cyclopropyl-5-fluoro-2,7-dioxo-1,3-dihydropyrido[2,3-f]quinoxaline-8-carboxylic acid
• CAS: 1338095-76-3
• 化学式: C₁₇H₁₄FN₃O₅
• 分子量: 359.314
• InChiKey: JLDLFJDGLDAKHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  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

文献信息

• Synthesis and antibacterial properties of new N₄-acetylated hexahydro-2,7-dioxopyrido[2,3-<i>f</i>]quinoxaline-8-carboxylic acids
  作者：Yusuf M. Al-Hiari、Ashok K. Shakya、Muhammed H. Alzweiri、Tariq M Al-Qirim、Ghassan Shattat、Mustafa M. El-Abadelah

  DOI：10.3109/14756366.2010.543421

  日期：2011.10.1

  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.