ethyl 2-(4-chlorophenyl)-4,7-dihydro-7-oxopyrazolo[1,5-a]pyrimidine-6-carboxylate | 331674-95-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 2-(4-chlorophenyl)-4,7-dihydro-7-oxopyrazolo[1,5-a]pyrimidine-6-carboxylate
• CAS: 331674-95-4
• 化学式: C₁₅H₁₂ClN₃O₃
• 分子量: 317.732
• InChiKey: ABQYAMGZFCKNNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.52
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  76.46
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-(4-chlorophenyl)-4,7-dihydro-7-oxopyrazolo[1,5-a]pyrimidine-6-carboxylate 在 水 、 potassium carbonate 、 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 2-(4-chlorophenyl)-4,7-dihydro-7-oxo-4-pentylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid
  参考文献：
  名称：

  Discovery of 7-Oxopyrazolo[1,5-a]pyrimidine-6-carboxamides as Potent and Selective CB₂ Cannabinoid Receptor Inverse Agonists

  摘要：

  We recently described the medicinal chemistry of a new series of heteroaryl-4-oxopyridine/7-oxopyrimidines as CB2 receptor partial agonists, showing that the functionality of these ligands is controlled by the nature of the heteroaryl function condensed with the pyridine ring. We describe herein the design and synthesis of the 7-oxopyrazolo[1,5-a]pyrimidine-6-carboxamides, structural isomers of our previously reported pyrazolo[3,4-Hpyridines. All of the new compounds showed high affinity and selectivity for the CB2 receptor in the nanomolar range. In 3,5-cyclic adenosine monophosphate (cAMP) assays, the novel series shows stimulatory effects on forskolin-induced cAMP production acting as inverse agonists.

  DOI：

  10.1021/jm400182t
• 作为产物：
  描述：

  乙氧基甲叉丙二酸二乙酯 、 3-(4-氯苯基)-1H-吡唑-5-胺 在 溶剂黄146 作用下， 反应 4.0h， 以70%的产率得到ethyl 2-(4-chlorophenyl)-4,7-dihydro-7-oxopyrazolo[1,5-a]pyrimidine-6-carboxylate
  参考文献：
  名称：

  Discovery of 7-Oxopyrazolo[1,5-a]pyrimidine-6-carboxamides as Potent and Selective CB₂ Cannabinoid Receptor Inverse Agonists

  摘要：

  We recently described the medicinal chemistry of a new series of heteroaryl-4-oxopyridine/7-oxopyrimidines as CB2 receptor partial agonists, showing that the functionality of these ligands is controlled by the nature of the heteroaryl function condensed with the pyridine ring. We describe herein the design and synthesis of the 7-oxopyrazolo[1,5-a]pyrimidine-6-carboxamides, structural isomers of our previously reported pyrazolo[3,4-Hpyridines. All of the new compounds showed high affinity and selectivity for the CB2 receptor in the nanomolar range. In 3,5-cyclic adenosine monophosphate (cAMP) assays, the novel series shows stimulatory effects on forskolin-induced cAMP production acting as inverse agonists.

  DOI：

  10.1021/jm400182t