Ethyl 4-[(1-amino-2-phenylethylidene)amino]-1-phenylpyrazole-3-carboxylate;hydrochloride | 1190306-07-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: Ethyl 4-[(1-amino-2-phenylethylidene)amino]-1-phenylpyrazole-3-carboxylate;hydrochloride
• CAS: 1190306-07-0
• 化学式: C₂₀H₂₀N₄O₂*ClH
• 分子量: 384.865
• InChiKey: WQHAUAZKSXYSAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  82.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl 4-[(1-amino-2-phenylethylidene)amino]-1-phenylpyrazole-3-carboxylate;hydrochloride 生成 5-benzyl-2-phenyl-2H-pyrazolo[4,3-d]pyrimidin-7(6H)-one
  参考文献：
  名称：

  2-Phenylpyrazolo[4,3-d]pyrimidin-7-one as a New Scaffold To Obtain Potent and Selective Human A₃ Adenosine Receptor Antagonists: New Insights into the Receptor−Antagonist Recognition

  摘要：

  A molecular simplification approach of previously reported 2-arylpyrazolo[3,4-c]quinolin-4-ones was applied to design 2-arylpyrazolo[4,3-d]pyrimidin-7-one derivatives as new human A(3) adenosine receptor antagonists. Substituents with different lipophilicity and steric hindrance were introduced at the 5-position of the bicyclic Scaffold (R-5 = H, Me, Et, Ph, CH2Ph) and on the 2-phenyl ring (OMe, Me). Most of the synthesized derivatives were highly potent hA(3) adenosine receptor antagonists, the best being the 2-(4-methoxyphenyl)pyrazolo[4,3-d]pyrimidin-7-one (K-i = 1.2 nM). The new compounds were also highly selective, being completely devoid of affinity toward hA(1), hA(2A), and hA(2B) adenosine receptors. On the basis of the recently published human A(2A) receptor crystallographic information, we propose it novel receptor-driven hypothesis to explain both A(3) AR affinity and A(3) versus A(2A) Selectivity profiles of these new antagonists.

  DOI：

  10.1021/jm900718w
• 作为产物：
  描述：

  ethyl 4-amino-1-phenyl-1H-pyrazole-3-carboxylate 、 苯乙腈 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 Ethyl 4-[(1-amino-2-phenylethylidene)amino]-1-phenylpyrazole-3-carboxylate;hydrochloride
  参考文献：
  名称：

  2-Phenylpyrazolo[4,3-d]pyrimidin-7-one as a New Scaffold To Obtain Potent and Selective Human A₃ Adenosine Receptor Antagonists: New Insights into the Receptor−Antagonist Recognition

  摘要：

  A molecular simplification approach of previously reported 2-arylpyrazolo[3,4-c]quinolin-4-ones was applied to design 2-arylpyrazolo[4,3-d]pyrimidin-7-one derivatives as new human A(3) adenosine receptor antagonists. Substituents with different lipophilicity and steric hindrance were introduced at the 5-position of the bicyclic Scaffold (R-5 = H, Me, Et, Ph, CH2Ph) and on the 2-phenyl ring (OMe, Me). Most of the synthesized derivatives were highly potent hA(3) adenosine receptor antagonists, the best being the 2-(4-methoxyphenyl)pyrazolo[4,3-d]pyrimidin-7-one (K-i = 1.2 nM). The new compounds were also highly selective, being completely devoid of affinity toward hA(1), hA(2A), and hA(2B) adenosine receptors. On the basis of the recently published human A(2A) receptor crystallographic information, we propose it novel receptor-driven hypothesis to explain both A(3) AR affinity and A(3) versus A(2A) Selectivity profiles of these new antagonists.

  DOI：

  10.1021/jm900718w