3-(4-isopropylphenyl)-7-methylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid | 941573-59-7

• 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)-7-methylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid
• 英文别名: 3-(4-Isopropylphenyl)-7-methylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid；7-methyl-3-(4-propan-2-ylphenyl)pyrazolo[1,5-a]pyrimidine-6-carboxylic acid
• CAS: 941573-59-7
• 化学式: C₁₇H₁₇N₃O₂
• 分子量: 295.341
• InChiKey: RITUGHQUNDVDTE-UHFFFAOYSA-N

物化性质

• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  67.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-isopropylphenyl)-7-methylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid 、 (S)-1-phenoxypropan-2-amine 在 1-羟基苯并三唑 、 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 12.0h， 生成 (S)-3-(4-isopropylphenyl)-7-methyl-N-(1-phenoxypropan-2-yl)pyrazolo[1,5-a]pyrimidine-6-carboxamide
  参考文献：
  名称：

  发现吡唑并嘧啶是高亲和力烟酸受体GPR109A的第一类变构激动剂。

  摘要：

  发现吡唑并嘧啶是高亲和力烟酸受体GPR109A的第一类变构激动剂。除了其固有活性外，化合物9n还显着增强了烟酸与受体的结合，从而增强了烟酸的功能功效。

  DOI：

  10.1016/j.bmcl.2008.08.039
• 作为产物：
  描述：

  2-乙氧亚甲基乙酰乙酸乙酯 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 为溶剂， 反应 19.0h， 生成 3-(4-isopropylphenyl)-7-methylpyrazolo[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

文献信息

• Discovery of pyrazolopyrimidines as the first class of allosteric agonists for the high affinity nicotinic acid receptor GPR109A
  作者：Hong C. Shen、Andrew K.P. Taggart、Larissa C. Wilsie、M. Gerard Waters、Milton L. Hammond、James R. Tata、Steven L. Colletti

  DOI：10.1016/j.bmcl.2008.08.039

  日期：2008.9

  Pyrazolopyrimidines were discovered as the first class of allosteric agonists for the high affinity nicotinic acid receptor GPR109A. In addition to its intrinsic activity, compound 9n significantly enhances nicotinic acid binding to the receptor, thereby potentiating the functional efficacy of nicotinic acid.

  发现吡唑并嘧啶是高亲和力烟酸受体GPR109A的第一类变构激动剂。除了其固有活性外，化合物9n还显着增强了烟酸与受体的结合，从而增强了烟酸的功能功效。
• Novel 3,6,7-Substituted Pyrazolopyrimidines as Positive Allosteric Modulators for the Hydroxycarboxylic Acid Receptor 2 (GPR109A)
  作者：Clara C. Blad、Jacobus P. D. van Veldhoven、Corné Klopman、Dieter R. Wolfram、Johannes Brussee、J. Robert Lane、Adriaan P. IJzerman

  DOI：10.1021/jm300164q

  日期：2012.4.12

  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.