4,7-dihydro-2-(furan-3-yl)-7-oxo-4-pentylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid | 1440807-17-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并嘧啶类
• 英文名称: 4,7-dihydro-2-(furan-3-yl)-7-oxo-4-pentylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid
• 英文别名: 2-(Furan-3-yl)-7-oxo-4-pentylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid；2-(furan-3-yl)-7-oxo-4-pentylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid
• CAS: 1440807-17-9
• 化学式: C₁₆H₁₇N₃O₄
• 分子量: 315.329
• InChiKey: DSCNJTMJADIPQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  88.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  金刚烷胺 、 4,7-dihydro-2-(furan-3-yl)-7-oxo-4-pentylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid 在 N,N-二异丙基乙胺 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 27.17h， 以53%的产率得到N-(1-adamantyl)-2-(furan-3-yl)-7-oxo-4-pentylpyrazolo[1,5-a]pyrimidine-6-carboxamide
  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：

  ethyl 4,7-dihydro-2-(furan-3-yl)-7-oxo-4-pentylpyrazolo[1,5-a]pyrimidine-6-carboxylate 在 水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以71%的产率得到4,7-dihydro-2-(furan-3-yl)-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

文献信息

• Discovery of 7-Oxopyrazolo[1,5-<i>a</i>]pyrimidine-6-carboxamides as Potent and Selective CB₂ Cannabinoid Receptor Inverse Agonists
  作者：Mojgan Aghazadeh Tabrizi、Pier Giovanni Baraldi、Giulia Saponaro、Allan R. Moorman、Romeo Romagnoli、Delia Preti、Stefania Baraldi、Emanuela Ruggiero、Cristina Tintori、Tiziano Tuccinardi、Fabrizio Vincenzi、Pier Andrea Borea、Katia Varani

  DOI：10.1021/jm400182t

  日期：2013.6.13

  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.