1-(2,3,5-tri-O-benzyl-α-D-arabinofuranosyl)-3-acetoxy-2-pyridone | 87597-97-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2,3,5-tri-O-benzyl-α-D-arabinofuranosyl)-3-acetoxy-2-pyridone
• CAS: 87597-97-5
• 化学式: C₃₃H₃₃NO₇
• 分子量: 555.628
• InChiKey: GVXRMBFYRSRTMO-QFBUMDDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.06
• 重原子数：
  41.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  85.22
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  2,3,5-Tri-O-benzyl-1-O-(p-nitrobenzoyl)-β-D-arabinofuranose 、 3-乙酰氧基-2(1H)-吡啶酮 、 乙酰氯 在 ammonium sulfate 、 三氟甲磺酸三甲基硅酯 、 三乙胺 、 六甲基二硅氮烷 作用下， 生成 1-(2,3,5-tri-O-benzyl-α-D-arabinofuranosyl)-3-acetoxy-2-pyridone 、 1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-3-acetoxy-2-pyridone
  参考文献：
  名称：

  Synthesis of 3-hydroxy-2- and -4-pyridone nucleosides as potential antitumor agents

  摘要：

  The ribo- and arabinofuranosyl nucleosides of antitumor active 2- and 4-pyridones 1a and 2a were prepared by direct condensation of the silylated bases with either 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose (4a) or 2,3,5-tri-O-benzyl-1-p-nitrobenzoyl-D-arabinofuranose (7) in the presence of trimethylsilyl triflate (Me3SiOTf). In the case of the arabinofuranosyl nucleosides, separation of the alpha and beta anomers was accomplished at the stage of O-benzyl-protected compounds (8b + 9b, and 10b + 11b) after chemical functionalization of the 3-hydroxy group of the pyridone aglycons with acetyl and benzyl groups, respectively. Deblocking of the protected ribo- and arabinofuranosyl nucleosides was performed by the standard methods. In vitro activity against P-388 cells in culture indicated that the 4-pyridone riboside 6d was the most active member of the series with a twofold lower ID50 than the parent pyridone 2a. However, this and all the other compounds tested in this series showed no activity against the in vivo model system of murine P-388 leukemia at doses ranging from 25 to 400 mg/kg qd 1-5.

  DOI：

  10.1021/jm00368a010