1-β-D-ribofuranosyl-3-hydroxy-2-methyl-4-pyridone | 87597-94-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-β-D-ribofuranosyl-3-hydroxy-2-methyl-4-pyridone
• 英文别名: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-hydroxy-2-methylpyridin-4-one
• CAS: 87597-94-2
• 化学式: C₁₁H₁₅NO₆
• 分子量: 257.243
• InChiKey: RYWYYPYGPHEYCG-QCNRFFRDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  111
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N,O-双(三甲基硅烷基)三氟乙酰胺 、 1-β-D-ribofuranosyl-3-hydroxy-2-methyl-4-pyridone 以 乙腈 为溶剂， 反应 1.0h， 生成 1-((2R,3R,4R,5R)-3,4-Bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-2-methyl-3-trimethylsilanyloxy-1H-pyridin-4-one
  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
• 作为产物：
  描述：

  1-乙酰氧基-2,3,5-三苯甲酰氧基-1-beta-D-呋喃核糖 在 palladium on activated charcoal 甲醇 、 氨 、 氢气 、 四氯化锡 作用下， 以 甲醇 、 水 、 溶剂黄146 、 1,2-二氯乙烷 为溶剂， 反应 4.0h， 生成 1-β-D-ribofuranosyl-3-hydroxy-2-methyl-4-pyridone
  参考文献：
  名称：

  Synthesis of 2-Alkyl-3-hydroxy-4-pyridinone-ribonucleosides, Potential Oral Iron Chelators

  摘要：

  Several ribonucleosides, named 2-alkyl-3-hydroxy-1-(beta-D-ribofuranosyl or pyranosyl)-4-pyridinones, were synthesized in good yield. The method provides a useful means to obtain alpha-ketohydroxypyridin derivatives with different sugar moieties that, if used as drugs, might enhance their absorption from the intestine and certain other desirable pharmacological properties.

  DOI：

  10.1080/15257779508010712

文献信息

• Synthesis of 3-hydroxy-2- and -4-pyridone nucleosides as potential antitumor agents
  作者：David T. Mao、John S. Driscoll、Victor E. Marquez

  DOI：10.1021/jm00368a010

  日期：1984.2

  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.
• Synthesis of 2-Alkyl-3-hydroxy-4-pyridinone-ribonucleosides, Potential Oral Iron Chelators
  作者：Gang Liu、Fred W. Bruenger、Amy M. Barrios、Scott C. Miller

  DOI：10.1080/15257779508010712

  日期：1995.11

  Several ribonucleosides, named 2-alkyl-3-hydroxy-1-(beta-D-ribofuranosyl or pyranosyl)-4-pyridinones, were synthesized in good yield. The method provides a useful means to obtain alpha-ketohydroxypyridin derivatives with different sugar moieties that, if used as drugs, might enhance their absorption from the intestine and certain other desirable pharmacological properties.