3-(4-isopropylphenyl)pyrazolo[1,5-a]pyrimidine-6-carboxylic acid | 1370287-44-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-isopropylphenyl)pyrazolo[1,5-a]pyrimidine-6-carboxylic acid
• 英文别名: Pyrazolo[1,5-a]pyrimidine-6-carboxylic acid, 3-[4-(1-methylethyl)phenyl]-；3-(4-propan-2-ylphenyl)pyrazolo[1,5-a]pyrimidine-6-carboxylic acid
• CAS: 1370287-44-7
• 化学式: C₁₆H₁₅N₃O₂
• 分子量: 281.314
• InChiKey: ORWPNGNFHRTMKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  67.49
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-(4-isopropylphenyl)pyrazolo[1,5-a]pyrimidine-6-carboxylic acid 、 2-苯氧基乙胺 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以59%的产率得到3-(4-isopropylphenyl)-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：

  4-(4-Isopropylphenyl)-1h-pyrazol-3-amine 在 5%-palladium/activated carbon 、 氢气 、 sodium acetate 、 N,N-二甲基苯胺 、 lithium hydroxide 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 为溶剂， 20.0 ℃ 、250.0 kPa 条件下， 反应 23.0h， 生成 3-(4-isopropylphenyl)pyrazolo[1,5-a]pyrimidine-6-carboxylic acid
  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