(2-甲基-4-氧代-1H-吡啶-3-基)乙酸酯 | 17184-20-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: (2-甲基-4-氧代-1H-吡啶-3-基)乙酸酯
• 英文名称: 2-methyl-3-acetoxy-4(1H)-pyridone
• 英文别名: 3-Acetoxy-2-methyl-4(1H)-pyridon；2-Methyl-3-acetoxy-4(1H)-pyridon；4(1H)-Pyridinone, 3-(acetyloxy)-2-methyl-；(2-methyl-4-oxo-1H-pyridin-3-yl) acetate
• CAS: 17184-20-2
• 化学式: C₈H₉NO₃
• 分子量: 167.164
• InChiKey: HIAASBFNGMVSOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2-甲基-4-氧代-1H-吡啶-3-基)乙酸酯 在 甲醇 、 ammonium sulfate 、 三氟甲磺酸三甲基硅酯 、 氨 、 六甲基二硅氮烷 作用下， 反应 194.0h， 生成 1-β-D-ribofuranosyl-3-hydroxy-2-methyl-4-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
• 作为产物：
  描述：

  3-甲氧基-2-甲基-1H-吡啶-4-酮 在 氢溴酸 作用下， 反应 25.0h， 生成 (2-甲基-4-氧代-1H-吡啶-3-基)乙酸酯
  参考文献：
  名称：

  吡啶酮作为潜在的抗肿瘤药II：3-乙酰氧基-2-吡啶酮的4-吡啶酮和生物等排体

  摘要：

  对抗鼠P-388白血病的活性的吡啶酮结构要求已扩展到3-羟基-4-吡啶酮的等规类似物，该化合物以前被发现具有活性。氨基可以取代3-羟基官能团并保持活性。硫而不是氨基官能团可以取代2-位的内酰胺氧。内酰胺氧从吡啶环中的2-位重定位也产生活性吡啶酮，包括2-甲基-3-乙酰氧基-4-吡啶酮。该化合物的T / C值为179％，是迄今为止在吡啶酮研究中发现的最具活性的物质。

  DOI：

  10.1002/jps.2600690923

文献信息

• Peratoner; Tamburello, Chemisches Zentralblatt, 1905, p. II,681
  作者：Peratoner、Tamburello

  DOI：——

  日期：——
• HWANG D. R.; PROCTOR G. R.; DRISCOLL J. S., J. PHARM. SCI., 1980, 69, NO 9, 1074-1076
  作者：HWANG D. R.、 PROCTOR G. R.、 DRISCOLL J. S.

  DOI：——

  日期：——
• 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.
• Pyridones as Potential Antitumor Agents II: 4-Pyridones and Bioisosteres of 3-Acetoxy-2-pyridone
  作者：Deng R. Hwang、George R. Proctor、John S. Driscoll

  DOI：10.1002/jps.2600690923

  日期：1980.9

  Pyridone structural requirements for activity against murine P-388 leukemia have been extended to isosteric analogs of 3-hydroxy-4-pyridone, a compound previously found to have activity. An amino group can be substituted for the 3-hydroxyl function with retention of activity. A sulfur, but not an amino function, can replace the lactam oxygen in the 2-position. Relocation of the lactam oxygen from the

  对抗鼠P-388白血病的活性的吡啶酮结构要求已扩展到3-羟基-4-吡啶酮的等规类似物，该化合物以前被发现具有活性。氨基可以取代3-羟基官能团并保持活性。硫而不是氨基官能团可以取代2-位的内酰胺氧。内酰胺氧从吡啶环中的2-位重定位也产生活性吡啶酮，包括2-甲基-3-乙酰氧基-4-吡啶酮。该化合物的T / C值为179％，是迄今为止在吡啶酮研究中发现的最具活性的物质。