N-(4-methoxyphenyl)-7-aminoheptan-4-one | 208646-36-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-(4-methoxyphenyl)-7-aminoheptan-4-one
• 英文别名: 1-(4-Methoxyanilino)heptan-4-one
• CAS: 208646-36-0
• 化学式: C₁₄H₂₁NO₂
• 分子量: 235.326
• InChiKey: IGXJCHHVINBCCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-methoxyphenyl)-7-aminoheptan-4-one 在 sodium hydroxide 、 sodium methylate 作用下， 以 甲醇 、 乙醇 、 苯 为溶剂， 反应 23.0h， 生成 1-(4-Fluoro-phenyl)-6-(4-methoxy-phenyl)-3-propyl-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：

  4-碘苯甲醚 在 铜 、 potassium carbonate 作用下， 以 乙醚 为溶剂， 反应 20.0h， 生成 N-(4-methoxyphenyl)-7-aminoheptan-4-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

文献信息

• 7-Oxo-4,5,6,7-tetrahydro-1<i>H</i>-pyrazolo[3,4-<i>c</i>]pyridines as Novel Inhibitors of Human Eosinophil Phosphodiesterase
  作者：Allen J. Duplantier、Catharine J. Andresen、John B. Cheng、Victoria L. Cohan、Christian Decker、Frank M. DiCapua、Kenneth G. Kraus、Kerry L. Johnson、Claudia R. Turner、John P. UmLand、John W. Watson、Ronald T. Wester、Alison S. Williams、John A. Williams

  DOI：10.1021/jm9800090

  日期：1998.6.1

  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).