5-氨基-1,3-二苄基-1H-吡唑-4-羧酸乙酯 | 1027843-43-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-氨基-1,3-二苄基-1H-吡唑-4-羧酸乙酯
• 英文名称: Ethyl 5-amino-1,3-dibenzylpyrazole-4-carboxylate
• CAS: 1027843-43-1
• 化学式: C₂₀H₂₁N₃O₂
• 分子量: 335.406
• InChiKey: YAOBMRZHSOGLDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-氨基-1,3-二苄基-1H-吡唑-4-羧酸乙酯 在 甲醇 、 磺酰氯 、 sodium methylate 、 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 64.0h， 生成 (rac)-(6aR*,9aS*)-1,3-bis(phenylmethyl)-5,6a,7,8,9,9a-hexahydro-5-methylcyclopent[4,5]imidazo[1,2-a]pyrazolo[4,3-e]pyrimidin-4(1H)-one
  参考文献：
  名称：

  Synthesis and Evaluation of Polycyclic Pyrazolo[3,4-d]pyrimidines as PDE1 and PDE5 cGMP Phosphodiesterase Inhibitors

  摘要：

  Polycyclic pyrazolo[3,4-d]pyrimidines (represented by 3 and 4) were synthesized as analogues of the recently reported polycyclic guanine phosphodiesterase (PDE) inhibitors. From the structure-activity relationship (SAR) development of a series of compounds, it was discovered that C-3 benzyl and N-2 methyl disubstitution on the pyrazole ring gave the best combination of potency and selectivity for PDE1 and PDE5 cGMP PDEs as represented by compound 4c: PDE1, IC50 = 60 nM; PDE3, IC50 = 55 000 nM; PDE5, IC50 = 75 nM. These compounds were also evaluated in vivo and found to be good orally active antihypertensives in laboratory animal models. Finally, comparisons were made of the in vitro and in vivo profiles of the pyrazolo[3,4-d]pyrimidine compound 4c with those of two representative guanine compounds.

  DOI：

  10.1021/jm970495b
• 作为产物：
  描述：

  (E)-2-Cyano-3-hydroxy-4-phenyl-but-2-enoic acid ethyl ester 在 三乙胺 、 silver carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 31.0h， 生成 5-氨基-1,3-二苄基-1H-吡唑-4-羧酸乙酯
  参考文献：
  名称：

  Synthesis and Evaluation of Polycyclic Pyrazolo[3,4-d]pyrimidines as PDE1 and PDE5 cGMP Phosphodiesterase Inhibitors

  摘要：

  Polycyclic pyrazolo[3,4-d]pyrimidines (represented by 3 and 4) were synthesized as analogues of the recently reported polycyclic guanine phosphodiesterase (PDE) inhibitors. From the structure-activity relationship (SAR) development of a series of compounds, it was discovered that C-3 benzyl and N-2 methyl disubstitution on the pyrazole ring gave the best combination of potency and selectivity for PDE1 and PDE5 cGMP PDEs as represented by compound 4c: PDE1, IC50 = 60 nM; PDE3, IC50 = 55 000 nM; PDE5, IC50 = 75 nM. These compounds were also evaluated in vivo and found to be good orally active antihypertensives in laboratory animal models. Finally, comparisons were made of the in vitro and in vivo profiles of the pyrazolo[3,4-d]pyrimidine compound 4c with those of two representative guanine compounds.

  DOI：

  10.1021/jm970495b