3-bromo-7-methyl-N-(2-phenoxyethyl)pyrazolo[1,5-a]pyrimidine-6-carboxamide | 1370287-62-9

• 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: 3-bromo-7-methyl-N-(2-phenoxyethyl)pyrazolo[1,5-a]pyrimidine-6-carboxamide
• CAS: 1370287-62-9
• 化学式: C₁₆H₁₅BrN₄O₂
• 分子量: 375.225
• InChiKey: RJSFQAAXGWQJQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-bromo-7-methyl-N-(2-phenoxyethyl)pyrazolo[1,5-a]pyrimidine-6-carboxamide 、 3,4-二氯苯硼酸 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 sodium carbonate 作用下， 以 水 、 甲苯 为溶剂， 反应 2.0h， 以45%的产率得到3-(3,4-dichlorophenyl)-7-methyl-N-(2-phenoxyethyl)pyrazolo[1,5-a]pyrimidine-6-carboxamide
  参考文献：
  名称：

  Novel 3,6,7-Substituted Pyrazolopyrimidines as Positive Allosteric Modulators for the Hydroxycarboxylic Acid Receptor 2 (GPR109A)

  摘要：

  A number of pyrazolopyrimidines were synthesized and tested for their positive allosteric modulation of the HCA(2) receptor (GPR109A). Compound 24, an efficacious and potent agonist and allosteric enhancer of nicotinic acid's action, was the basis for most other compounds. Interestingly, some of the compounds were found to increase the efficacy of the endogenous ligand 3-hydroxybutyrate and enhance its potency almost 10-fold. This suggests that the pyrazolopyrimidines may have therapeutic value when given alone.

  DOI：

  10.1021/jm300164q
• 作为产物：
  描述：

  2-乙氧亚甲基乙酰乙酸乙酯 在 N-溴代丁二酰亚胺(NBS) 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 40.5h， 生成 3-bromo-7-methyl-N-(2-phenoxyethyl)pyrazolo[1,5-a]pyrimidine-6-carboxamide
  参考文献：
  名称：

  Novel 3,6,7-Substituted Pyrazolopyrimidines as Positive Allosteric Modulators for the Hydroxycarboxylic Acid Receptor 2 (GPR109A)

  摘要：

  A number of pyrazolopyrimidines were synthesized and tested for their positive allosteric modulation of the HCA(2) receptor (GPR109A). Compound 24, an efficacious and potent agonist and allosteric enhancer of nicotinic acid's action, was the basis for most other compounds. Interestingly, some of the compounds were found to increase the efficacy of the endogenous ligand 3-hydroxybutyrate and enhance its potency almost 10-fold. This suggests that the pyrazolopyrimidines may have therapeutic value when given alone.

  DOI：

  10.1021/jm300164q