3-hydroxy-2-oxo-1-phenyl-4-valeryl-1,2,5,6-tetrahydropyridine | 208646-38-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-hydroxy-2-oxo-1-phenyl-4-valeryl-1,2,5,6-tetrahydropyridine
• 英文别名: 5-Hydroxy-4-pentanoyl-1-phenyl-2,3-dihydropyridin-6-one
• CAS: 208646-38-2
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: AHHXFFMOMQNMMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-氟苯肼盐酸盐 、 3-hydroxy-2-oxo-1-phenyl-4-valeryl-1,2,5,6-tetrahydropyridine 在 sodium methylate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 20.0h， 以44%的产率得到3-Butyl-1-(4-fluoro-phenyl)-6-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
• 作为产物：
  描述：

  1-苯基-2-吡咯烷酮 在 sodium hydroxide 、 sodium methylate 作用下， 以 甲醇 、 乙醚 、 乙醇 、 苯 为溶剂， 反应 5.0h， 生成 3-hydroxy-2-oxo-1-phenyl-4-valeryl-1,2,5,6-tetrahydropyridine
  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