3-ethyl-1-(4-fluoro-phenyl)-6-(4-methoxy-phenyl)-1,4,5,6-tetrahydro-pyrazolo[3,4-c]pyridin-7-one | 6497-50-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-ethyl-1-(4-fluoro-phenyl)-6-(4-methoxy-phenyl)-1,4,5,6-tetrahydro-pyrazolo[3,4-c]pyridin-7-one
• 英文别名: 3-Ethyl-1-(4-fluorophenyl)-6-(4-methoxyphenyl)-4,5-dihydropyrazolo[3,4-c]pyridin-7-one
• CAS: 6497-50-3
• 化学式: C₂₁H₂₀FN₃O₂
• 分子量: 365.407
• InChiKey: NDCHZUCLIAQWCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(4-甲氧基苯基)吡咯烷-2-酮 在 sodium hydroxide 、 sodium methylate 作用下， 以 甲醇 、 乙醚 、 乙醇 、 1,2-二氯乙烷 、 苯 为溶剂， 反应 7.75h， 生成 3-ethyl-1-(4-fluoro-phenyl)-6-(4-methoxy-phenyl)-1,4,5,6-tetrahydro-pyrazolo[3,4-c]pyridin-7-one
  参考文献：
  名称：

  7-Oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridines as Novel Inhibitors of Human Eosinophil Phosphodiesterase

  摘要：

  High-throughput file screening against inhibition of human lung PDE4 led to the discovery of 3-ethyl-1-(4-fluorophenyl)-6-phenyl-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine (11) as a novel PDE4 inhibitor. Subsequent SAR development, using an eosinophil PDE assay, led to analogues up to 50-fold more potent than 11 with IC50 values of 0.03-1.6 mu M. One such compound, CP-220,629 (22) (IC50 = 0.44 mu M), was efficacious in the guinea pig aerosolized antigen induced airway obstruction assay (ED50 2.0 mg/kg, po) and demonstrated a significant reduction in eosinophil (55%), neutrophil (65%), and IL-1 beta (82%) responses to antigen challenge in atopic monkeys (10 mg/kg, po).

  DOI：

  10.1021/jm9800090