5-(4-氟苯基)-4-氧代-4H-吡喃-3-羧酸 | 1052114-99-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-(4-氟苯基)-4-氧代-4H-吡喃-3-羧酸
• 英文名称: 5-(4-fluorophenyl)-4-oxo-4H-pyran-3-carboxylic acid
• 英文别名: 5-(4-Fluorophenyl)-4-oxopyran-3-carboxylic acid
• CAS: 1052114-99-4
• 化学式: C₁₂H₇FO₄
• 分子量: 234.184
• InChiKey: FVNLBOFQRSXTPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(4-氟苯基)-4-氧代-4H-吡喃-3-羧酸 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 生成 5-(4-fluorophenyl)-4-oxo-4H-pyran-3-carbonyl chloride
  参考文献：
  名称：

  Discovery of Pyrrolopyridine−Pyridone Based Inhibitors of Met Kinase: Synthesis, X-ray Crystallographic Analysis, and Biological Activities

  摘要：

  Conformationally constrained 2-pyridone analogue 2 is a potent Met kinase inhibitor with an IC(50) value of 1.8 nM. Further SAR of the 2-pyridone based inhibitors of Met kinase led to potent 4-pyridone and pyridine N-oxide inhibitors Such as 3 and 4. The X-ray crystallographic data of the inhibitor 2 bound to the ATP binding site of Met kinase protein provided insight into the binding modes of these inhibitors, and the SAR of this series of analogues was rationalized. Many of these analogues showed potent anti proliferative activities against the Met dependent GTL-16 gastric carcinoma cell line. Compound 2 also inhibited Flt-3 and VEGFR-2 kinases with IC(50) values of 4 and 27 nM, respectively. It possesses a favorable pharmacokinetic profile in mice and demonstrates significant in vivo antitumor activity in the GTI-16 human gastric carcinoma xenograft model.

  DOI：

  10.1021/jm800476q
• 作为产物：
  描述：

  5-(4-fluorophenyl)-4-oxo-4H-pyran-3-carbaldehyde 在 oxone 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以78%的产率得到5-(4-氟苯基)-4-氧代-4H-吡喃-3-羧酸
  参考文献：
  名称：

  Discovery of Pyrrolopyridine−Pyridone Based Inhibitors of Met Kinase: Synthesis, X-ray Crystallographic Analysis, and Biological Activities

  摘要：

  Conformationally constrained 2-pyridone analogue 2 is a potent Met kinase inhibitor with an IC(50) value of 1.8 nM. Further SAR of the 2-pyridone based inhibitors of Met kinase led to potent 4-pyridone and pyridine N-oxide inhibitors Such as 3 and 4. The X-ray crystallographic data of the inhibitor 2 bound to the ATP binding site of Met kinase protein provided insight into the binding modes of these inhibitors, and the SAR of this series of analogues was rationalized. Many of these analogues showed potent anti proliferative activities against the Met dependent GTL-16 gastric carcinoma cell line. Compound 2 also inhibited Flt-3 and VEGFR-2 kinases with IC(50) values of 4 and 27 nM, respectively. It possesses a favorable pharmacokinetic profile in mice and demonstrates significant in vivo antitumor activity in the GTI-16 human gastric carcinoma xenograft model.

  DOI：

  10.1021/jm800476q