(S)-N-((3-(4-(4-(3-azidopropyl)piperazin-1-yl)-3-fluorophenyl)-2-oxooxazolidin-5-yl)methyl)acetamide | 1622399-51-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (S)-N-((3-(4-(4-(3-azidopropyl)piperazin-1-yl)-3-fluorophenyl)-2-oxooxazolidin-5-yl)methyl)acetamide
• CAS: 1622399-51-2
• 化学式: C₁₉H₂₆FN₇O₃
• 分子量: 419.459
• InChiKey: KNPHMUKRYVSPIH-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.11
• 重原子数：
  30.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  113.88
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-N-((3-(4-(4-(3-azidopropyl)piperazin-1-yl)-3-fluorophenyl)-2-oxooxazolidin-5-yl)methyl)acetamide 、 2-丙炔-1-醇 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 甲醇 、 水 为溶剂， 反应 16.0h， 以49%的产率得到(S)-N-((3-(3-fluoro-4-(4-(3-(4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)propyl)piper-azin-1-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide
  参考文献：
  名称：

  An azido-oxazolidinone antibiotic for live bacterial cell imaging and generation of antibiotic variants

  摘要：

  An azide-functionalised analogue of the oxazolidinone antibiotic linezolid was synthesised and shown to retain antimicrobial activity. Using facile 'click' chemistry, this versatile intermediate can be further functionalised to explore antimicrobial structure-activity relationships or conjugated to fluorophores to generate fluorescent probes. Such probes can report bacteria and their location in a sample in real time. Modelling of the structures bound to the cognate 50S ribosome target demonstrates binding to the same site as linezolid is possible. The fluorescent probes were successfully used to image Gram-positive bacteria using confocal microscopy.

  DOI：

  10.1016/j.bmc.2014.05.054
• 作为产物：
  描述：

  (R)-benzyl 4-(2-fluoro-4-(2-oxo-5-(tosyloxymethyl)oxazolidin-3-yl)phenyl)piperazine-1-carboxylate 在 吡啶 、 palladium 10% on activated carbon 、 氢气 、 三乙胺 、 甲胺 、 sodium iodide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 6.0h， 生成 (S)-N-((3-(4-(4-(3-azidopropyl)piperazin-1-yl)-3-fluorophenyl)-2-oxooxazolidin-5-yl)methyl)acetamide
  参考文献：
  名称：

  An azido-oxazolidinone antibiotic for live bacterial cell imaging and generation of antibiotic variants

  摘要：

  An azide-functionalised analogue of the oxazolidinone antibiotic linezolid was synthesised and shown to retain antimicrobial activity. Using facile 'click' chemistry, this versatile intermediate can be further functionalised to explore antimicrobial structure-activity relationships or conjugated to fluorophores to generate fluorescent probes. Such probes can report bacteria and their location in a sample in real time. Modelling of the structures bound to the cognate 50S ribosome target demonstrates binding to the same site as linezolid is possible. The fluorescent probes were successfully used to image Gram-positive bacteria using confocal microscopy.

  DOI：

  10.1016/j.bmc.2014.05.054