5-methoxy-1-(4-bromophenyl)-1H-pyrazole-3-carboxylic acid | 263237-96-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-methoxy-1-(4-bromophenyl)-1H-pyrazole-3-carboxylic acid
• 英文别名: 1-(4-Bromophenyl)-5-methoxy-1H-pyrazole-3-carboxylic acid；1-(4-bromophenyl)-5-methoxypyrazole-3-carboxylic acid
• CAS: 263237-96-3
• 化学式: C₁₁H₉BrN₂O₃
• 分子量: 297.108
• InChiKey: BBAQOKRFHUCEPU-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：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  64.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-methoxy-1-(4-bromophenyl)-1H-pyrazole-3-carboxylic acid 在 titanium(IV) isopropylate 、 四(三苯基膦)钯 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-(3-((R)-1((R)-(3-chlorophenyl)ethylanamino)ethyl)-5-methoxy-1H-pyrazol-1-yl)benzonitrile
  参考文献：
  名称：

  Discovery and Optimization of Substituted 1-(1-Phenyl-1H-pyrazol-3-yl)methanamines as Potent and Efficacious Type II Calcimimetics

  摘要：

  Our efforts to discover potent, orally bioavailable type II calcimimetic agents for the treatment of secondary hyperparathyroidism focused on the development of ring constrained analogues of the known calcimimetic R-568. The structure-activity relationships of various substituted heterocycles and their effects oil the human calcium-sensing receptor are discussed. Pyrazole 15 was shown to be efficacious in a rat in vivo pharmacodynamic model.

  DOI：

  10.1021/jm9012278
• 作为产物：
  描述：

  methyl 5-methoxy-1-(4-bromophenyl)-1H-pyrazole-3-carboxylate 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以93%的产率得到5-methoxy-1-(4-bromophenyl)-1H-pyrazole-3-carboxylic acid
  参考文献：
  名称：

  Discovery and Optimization of Substituted 1-(1-Phenyl-1H-pyrazol-3-yl)methanamines as Potent and Efficacious Type II Calcimimetics

  摘要：

  Our efforts to discover potent, orally bioavailable type II calcimimetic agents for the treatment of secondary hyperparathyroidism focused on the development of ring constrained analogues of the known calcimimetic R-568. The structure-activity relationships of various substituted heterocycles and their effects oil the human calcium-sensing receptor are discussed. Pyrazole 15 was shown to be efficacious in a rat in vivo pharmacodynamic model.

  DOI：

  10.1021/jm9012278

文献信息

• Discovery and Optimization of Substituted 1-(1-Phenyl-1<i>H</i>-pyrazol-3-yl)methanamines as Potent and Efficacious Type II Calcimimetics
  作者：Steve F. Poon、David J. St. Jean、Paul E. Harrington、Charles Henley、James Davis、Sean Morony、Fred D. Lott、Jeff D. Reagan、Jenny Ying-Lin Lu、Yuhua Yang、Christopher Fotsch

  DOI：10.1021/jm9012278

  日期：2009.11.12

  Our efforts to discover potent, orally bioavailable type II calcimimetic agents for the treatment of secondary hyperparathyroidism focused on the development of ring constrained analogues of the known calcimimetic R-568. The structure-activity relationships of various substituted heterocycles and their effects oil the human calcium-sensing receptor are discussed. Pyrazole 15 was shown to be efficacious in a rat in vivo pharmacodynamic model.