5-Hydroxy-2-(3-hydroxy-phenyl)-6-methoxy-pyrimidine-4-carboxylic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-Hydroxy-2-(3-hydroxy-phenyl)-6-methoxy-pyrimidine-4-carboxylic acid
• 英文别名: 5-Hydroxy-2-(3-hydroxyphenyl)-6-methoxy-pyrimidine-4-carboxylic acid；5-hydroxy-2-(3-hydroxyphenyl)-6-methoxypyrimidine-4-carboxylic acid
• 化学式: C₁₂H₁₀N₂O₅
• 分子量: 262.222
• InChiKey: QGYWVGBIPCUSLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  碘甲烷 、 methyl 5-(benzoyloxy)-6-hydroxy-2-{3-[(4-methoxybenzyl)oxy]phenyl}pyrimidine-4-carboxylate 在 caesium carbonate 、 三氟乙酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲醇 为溶剂， 反应 5.5h， 生成 5-Hydroxy-2-(3-hydroxy-phenyl)-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid 、 5-Hydroxy-2-(3-hydroxy-phenyl)-6-methoxy-pyrimidine-4-carboxylic acid
  参考文献：
  名称：

  HCV NS5b RNA-Dependent RNA Polymerase Inhibitors:  From α,γ-Diketoacids to 4,5-Dihydroxypyrimidine- or 3-Methyl-5- hydroxypyrimidinonecarboxylic Acids. Design and Synthesis

  摘要：

  A new class of the HCV NS5b RNA-dependent RNA polymerase inhibitors, the dihyroxypyrimidinecarboxylic acid derivative, was designed from a diketoacid and meconic acid derivative discovered by screening. Mechanism of action and essential moieties required for activity were identified. The corresponding N-methylpyrimidinone was also prepared; both classes are novel, reversible, and selective inhibitors of the HCV NS5b polymerase with improved druglike characteristics.

  DOI：

  10.1021/jm0494669

文献信息

• HCV NS5b RNA-Dependent RNA Polymerase Inhibitors:  From α,γ-Diketoacids to 4,5-Dihydroxypyrimidine- or 3-Methyl-5- hydroxypyrimidinonecarboxylic Acids. Design and Synthesis
  作者：Vincenzo Summa、Alessia Petrocchi、Victor G. Matassa、Marina Taliani、Ralph Laufer、Raffaele De Francesco、Sergio Altamura、Paola Pace

  DOI：10.1021/jm0494669

  日期：2004.10.1

  A new class of the HCV NS5b RNA-dependent RNA polymerase inhibitors, the dihyroxypyrimidinecarboxylic acid derivative, was designed from a diketoacid and meconic acid derivative discovered by screening. Mechanism of action and essential moieties required for activity were identified. The corresponding N-methylpyrimidinone was also prepared; both classes are novel, reversible, and selective inhibitors of the HCV NS5b polymerase with improved druglike characteristics.