(S)-4-acetyl-10-cyclopropyl-5-fluoro-1,2,3,4,7,10-hexahydro-3-isopropyl-2,7-dioxopyrido[2,3-f]quinoxaline-8-carboxylic acid | 1338095-78-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (S)-4-acetyl-10-cyclopropyl-5-fluoro-1,2,3,4,7,10-hexahydro-3-isopropyl-2,7-dioxopyrido[2,3-f]quinoxaline-8-carboxylic acid
• 英文别名: (3S)-4-acetyl-10-cyclopropyl-5-fluoro-2,7-dioxo-3-propan-2-yl-1,3-dihydropyrido[2,3-f]quinoxaline-8-carboxylic acid
• CAS: 1338095-78-5
• 化学式: C₂₀H₂₀FN₃O₅
• 分子量: 401.394
• InChiKey: OTNDIEACGGLKGF-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 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-氯-1-环丙基-6-氟-8-硝基-4-氧代-1,4-二氢喹啉-3-羧酸 在 sodium dithionite 、 碳酸氢钠 、 potassium carbonate 、 三乙胺 作用下， 以 乙醇 、 水 为溶剂， 反应 168.42h， 生成 (S)-4-acetyl-10-cyclopropyl-5-fluoro-1,2,3,4,7,10-hexahydro-3-isopropyl-2,7-dioxopyrido[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.