3-(4-fluorophenyl)-6,7-dimethyl-2-(4-methylsulfonylphenyl)pyrazolo[1,5-a]pyrimidine | 328554-03-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-fluorophenyl)-6,7-dimethyl-2-(4-methylsulfonylphenyl)pyrazolo[1,5-a]pyrimidine
• CAS: 328554-03-6
• 化学式: C₂₁H₁₈FN₃O₂S
• 分子量: 395.457
• InChiKey: WHGZGEFGZXHTST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  72.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-fluorophenyl)-6,7-dimethyl-2-(4-methylsulfonylphenyl)pyrazolo[1,5-a]pyrimidine 在 potassium permanganate 、 硫酸 、 三乙胺 作用下， 以 氯仿 、 水 为溶剂， 反应 72.0h， 以33%的产率得到[3-(4-Fluorophenyl)-6-methyl-2-(4-methylsulfonylphenyl)pyrazolo[1,5-a]pyrimidin-7-yl]methanol
  参考文献：
  名称：

  Synthesis and SAR of a New Series of COX-2-Selective Inhibitors:  Pyrazolo[1,5-a]pyrimidines

  摘要：

  The synthesis and pharmacological activity of a series of bicyclic pyrazolo[1,5-a]pyrimidines as potent and selective cyclooxygenase-2 (COX-2) inhibitors are described. The new compounds were evaluated both in vitro (COX-1 and COX-2 inhibition in human whole blood) and in vive (carrageenan-induced paw edema and air-pouch model). Modification of the pyrimidine substituents showed that 6,7-disubstitution provided the best activity and led to the identification of 3-(4-fluorophenyl)-6,7-dimethyl-2-(4-methylsulfonylphenyl)pyrazolo[1,5-a]pyrimidine (10f) as one of the most potent and selective COX-2 inhibitor in this series.

  DOI：

  10.1021/jm0009383
• 作为产物：
  描述：

  2-(4-fluorophenyl)-1-(4-(methylsulfonyl)phenyl)ethanone 在 盐酸 、 一水合肼 、 三氯氧磷 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 44.25h， 生成 3-(4-fluorophenyl)-6,7-dimethyl-2-(4-methylsulfonylphenyl)pyrazolo[1,5-a]pyrimidine
  参考文献：
  名称：

  Synthesis and SAR of a New Series of COX-2-Selective Inhibitors:  Pyrazolo[1,5-a]pyrimidines

  摘要：

  The synthesis and pharmacological activity of a series of bicyclic pyrazolo[1,5-a]pyrimidines as potent and selective cyclooxygenase-2 (COX-2) inhibitors are described. The new compounds were evaluated both in vitro (COX-1 and COX-2 inhibition in human whole blood) and in vive (carrageenan-induced paw edema and air-pouch model). Modification of the pyrimidine substituents showed that 6,7-disubstitution provided the best activity and led to the identification of 3-(4-fluorophenyl)-6,7-dimethyl-2-(4-methylsulfonylphenyl)pyrazolo[1,5-a]pyrimidine (10f) as one of the most potent and selective COX-2 inhibitor in this series.

  DOI：

  10.1021/jm0009383