4-(2,2-Diethoxyethyl)-2-phenylpyrazolo[1,5-a]pyrimidin-7(4H)-one | 86969-19-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(2,2-Diethoxyethyl)-2-phenylpyrazolo[1,5-a]pyrimidin-7(4H)-one
• 英文别名: 4-(2,2-diethoxyethyl)-2-phenylpyrazolo[1,5-a]pyrimidin-7-one
• CAS: 86969-19-9
• 化学式: C₁₈H₂₁N₃O₃
• 分子量: 327.383
• InChiKey: UHRYBVFXYCAJTH-UHFFFAOYSA-N

物化性质

• 沸点：
  499.6±55.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  56.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4,7-dihydro-2-phenylpyrazolo[1,5-a]pyrimidin-7-one 、 氯乙醛缩二乙醇 在 potassium carbonate 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以24%的产率得到4-(2,2-Diethoxyethyl)-2-phenylpyrazolo[1,5-a]pyrimidin-7(4H)-one
  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