5-Methyl-2-phenylpyrazolo[4,3-d]pyrimidin-7-amine | 1426541-23-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-Methyl-2-phenylpyrazolo[4,3-d]pyrimidin-7-amine
• 英文别名: 5-methyl-2-phenylpyrazolo[4,3-d]pyrimidin-7-amine
• CAS: 1426541-23-2
• 化学式: C₁₂H₁₁N₅
• 分子量: 225.253
• InChiKey: VCJVBLBICBKOAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  69.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  苯乙酸 、 5-Methyl-2-phenylpyrazolo[4,3-d]pyrimidin-7-amine 在 4-二甲氨基吡啶 、 1-hydroxybenzotriazole hydrochloride 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 168.0h， 以20%的产率得到N-(5-methyl-2-phenylpyrazolo[4,3-d]pyrimidin-7-yl)-2-phenylacetamide
  参考文献：
  名称：

  2-Arylpyrazolo[4,3-d]pyrimidin-7-amino Derivatives As New Potent and Selective Human A₃ Adenosine Receptor Antagonists. Molecular Modeling Studies and Pharmacological Evaluation

  摘要：

  On the basis of our previously reported 2-arylpyrazolo[4,3-d]pyrimidin-7-ones, a set of 2-arylpyrazolo[4,3- d]pyrimidin-7-amines were designed as new human (h) A(3) adenosine receptor (AR) antagonists. Lipophilic groups with different steric bulk were introduced at the 5-position of the bicyclic scaffold (R-5 = Me, Ph, CH2Ph), and different acyl and carbamoyl moieties (R-7) were appended on the 7-amino group, as well as a para-methoxy group inserted on the 2-phenyl ring. The presence of acyl groups turned out to be of paramount importance for an efficient and selective binding at the hA(3) AR In fact, most of the 7-acylamino derivatives showed low nanomolar affinity (K-l, = 2.5-45 nM) and high selectivity toward this receptor. A few selected pyrazolo[4,3-d]pyrimidin-7-amides were effective in counteracting oxaliplatin-induced apoptosis in rat astrocyte cell cultures, an in vitro model of neurotoxicity. Through an in silica receptor-driven approach the obtained binding data were rationalized and the molecular bases of the observed hA(3) AR affinity and hA(3) versus hA(2A) AR selectivity were explained.

  DOI：

  10.1021/jm400068e
• 作为产物：
  描述：

  3-ethoxycarbonyl-4-nitro-1-phenylpyrazole 在 palladium 10% on activated carbon 、 ammonium acetate 、 氨 、 环己烯 、 三氯氧磷 作用下， 以 乙醇 、 水 为溶剂， 反应 49.58h， 生成 5-Methyl-2-phenylpyrazolo[4,3-d]pyrimidin-7-amine
  参考文献：
  名称：

  2-Arylpyrazolo[4,3-d]pyrimidin-7-amino Derivatives As New Potent and Selective Human A₃ Adenosine Receptor Antagonists. Molecular Modeling Studies and Pharmacological Evaluation

  摘要：

  On the basis of our previously reported 2-arylpyrazolo[4,3-d]pyrimidin-7-ones, a set of 2-arylpyrazolo[4,3- d]pyrimidin-7-amines were designed as new human (h) A(3) adenosine receptor (AR) antagonists. Lipophilic groups with different steric bulk were introduced at the 5-position of the bicyclic scaffold (R-5 = Me, Ph, CH2Ph), and different acyl and carbamoyl moieties (R-7) were appended on the 7-amino group, as well as a para-methoxy group inserted on the 2-phenyl ring. The presence of acyl groups turned out to be of paramount importance for an efficient and selective binding at the hA(3) AR In fact, most of the 7-acylamino derivatives showed low nanomolar affinity (K-l, = 2.5-45 nM) and high selectivity toward this receptor. A few selected pyrazolo[4,3-d]pyrimidin-7-amides were effective in counteracting oxaliplatin-induced apoptosis in rat astrocyte cell cultures, an in vitro model of neurotoxicity. Through an in silica receptor-driven approach the obtained binding data were rationalized and the molecular bases of the observed hA(3) AR affinity and hA(3) versus hA(2A) AR selectivity were explained.

  DOI：

  10.1021/jm400068e