N-[2-(4-methoxyphenyl)-5-phenylpyrazolo[4,3-d]pyrimidin-7-yl]benzamide | 1426541-48-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-[2-(4-methoxyphenyl)-5-phenylpyrazolo[4,3-d]pyrimidin-7-yl]benzamide
• CAS: 1426541-48-1
• 化学式: C₂₅H₁₉N₅O₂
• 分子量: 421.458
• InChiKey: SLBHWADPYWJYRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  81.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  Ethyl 1-(4-methoxyphenyl)-4-nitropyrazole-3-carboxylate 在 吡啶 、 palladium 10% on activated carbon 、 ammonium acetate 、 氨 、 环己烯 、 三氯氧磷 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 30.14h， 生成 N-[2-(4-methoxyphenyl)-5-phenylpyrazolo[4,3-d]pyrimidin-7-yl]benzamide
  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