2-(4-methylphenyl)-5-methylpyrazolo[1,5-α]pyrimidin-3-ylacetic acid | 869334-92-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-methylphenyl)-5-methylpyrazolo[1,5-α]pyrimidin-3-ylacetic acid
• 英文别名: 2-[5-Methyl-2-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-3-yl]acetic acid
• CAS: 869334-92-9
• 化学式: C₁₆H₁₅N₃O₂
• 分子量: 281.314
• InChiKey: KEWLHODWLBEMNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  2-(4-methylphenyl)-5-methylpyrazolo[1,5-α]pyrimidin-3-ylacetic acid 、 二甲胺 在 三乙胺 、 氯甲酸乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以34%的产率得到N,N-dimethyl-2-[5-methyl-2-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-3-yl]acetamide
  参考文献：
  名称：

  A Novel Selective GABA_A α1 Receptor Agonist Displaying Sedative and Anxiolytic-like Properties in Rodents

  摘要：

  In our pursuit to identify selective ligands for Bz/GABA(A) receptor subtypes, a novel pyrazolo[1,5-a]pyrimidine derivative (4), the azaisostere of zolpidem, was synthesized and evaluated in vitro on bovine brain homogenate and on recombinant benzodiazepine receptors (alpha x beta 2/3 gamma 2, x = 1-3, 5) expressed in HEK293 cells. Compound 4 displayed affinity only for alpha 1 beta 2 gamma 2 subtype (K-i = 31 nM), and in an in-depth, in vivo study it revealed sedative and anxiolytic-like properties without any amnesic and myorelaxant effects in rodents.

  DOI：

  10.1021/jm058002n
• 作为产物：
  描述：

  对甲苯酰乙腈 在 lithium hydroxide 、 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 2-(4-methylphenyl)-5-methylpyrazolo[1,5-α]pyrimidin-3-ylacetic acid
  参考文献：
  名称：

  A Novel Selective GABA_A α1 Receptor Agonist Displaying Sedative and Anxiolytic-like Properties in Rodents

  摘要：

  In our pursuit to identify selective ligands for Bz/GABA(A) receptor subtypes, a novel pyrazolo[1,5-a]pyrimidine derivative (4), the azaisostere of zolpidem, was synthesized and evaluated in vitro on bovine brain homogenate and on recombinant benzodiazepine receptors (alpha x beta 2/3 gamma 2, x = 1-3, 5) expressed in HEK293 cells. Compound 4 displayed affinity only for alpha 1 beta 2 gamma 2 subtype (K-i = 31 nM), and in an in-depth, in vivo study it revealed sedative and anxiolytic-like properties without any amnesic and myorelaxant effects in rodents.

  DOI：

  10.1021/jm058002n