2-Propenoic acid, 3-(7-oxo-2-phenylpyrazolo[1,5-a]pyrimidin-4(7H)-yl)-,ethyl ester | 86969-21-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-Propenoic acid, 3-(7-oxo-2-phenylpyrazolo[1,5-a]pyrimidin-4(7H)-yl)-,ethyl ester
• 英文别名: ethyl 3-(4,7-dihydro-7-oxo-2-phenylpyrazolo<1,5-a>pyrimidin-4-yl)propenoate
• CAS: 86969-21-3
• 化学式: C₁₇H₁₅N₃O₃
• 分子量: 309.324
• InChiKey: FSMNJRWVFJHNLS-UHFFFAOYSA-N

物化性质

• 沸点：
  500.1±60.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  65.6
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  4,7-dihydro-2-phenylpyrazolo[1,5-a]pyrimidin-7-one 、 丙炔酸乙酯 反应 5.0h， 以30%的产率得到2-Propenoic acid, 3-(7-oxo-2-phenylpyrazolo[1,5-a]pyrimidin-4(7H)-yl)-,ethyl ester
  参考文献：
  名称：

  2-Phenylpyrazolo[1,5-a]pyrimidin-7-ones. A new class of nonsteroidal antiinflammatory drugs devoid of ulcerogenic activity

  摘要：

  Syntheses of some pyrazolo[1,5-a]pyrimidines were performed in order to study the relationship between structural modifications on the parent 4,7-dihydro-2-phenylpyrazolo[1,5-a]pyrimidin-7-one (1) and their antiinflammatory properties. The modifications carried out were introduction and functionalization of a longer side chain at the 4-position, substitution of the hydrogen atom at the 3-position, and replacement of the phenyl group with a 4-methylphenyl, methyl, or hydrogen substituent. 4-Ethyl-4,7-dihydro-2-phenylpyrazolo [1,5-a]pyrimidin-7-one (3) showed the highest activity and a better therapeutic index than phenylbutazone and indomethacin, used as reference drugs. All other changes at the 3-, 5-, and 6-positions, as well as the replacement of the phenyl group at position 2, caused a marked decrease of activity. Compound 3 was found devoid of ulcerogenic activity and was probably endowed with antiulcerogenic properties.

  DOI：

  10.1021/jm00366a009