5-氨基-3-苄基-1-甲基-1H-吡唑-4-羧酸乙酯 | 1027994-06-4

• 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-3-苄基-1-甲基-1H-吡唑-4-羧酸乙酯
• 英文名称: Ethyl 5-amino-3-benzyl-1-methylpyrazole-4-carboxylate
• CAS: 1027994-06-4
• 化学式: C₁₄H₁₇N₃O₂
• 分子量: 259.308
• InChiKey: QQTJFAFLCKZXNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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-3-苄基-1-甲基-1H-吡唑-4-羧酸乙酯 在 甲醇 、 sodium methylate 、 三乙胺 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 3-Benzyl-1,5-dimethyl-1,7-dihydro-pyrazolo[3,4-d]pyrimidine-4,6-dione
  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-3-苄基-1-甲基-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

文献信息

• KAT ll INHIBITORS
  申请人：Dounay Amy B.

  公开号：US20120302599A1

  公开（公告）日：2012-11-29

  Compounds of Formula I: wherein X, Y, Z, R 1 , R 2 , R 3 , R 4 are as defined herein, and pharmaceutically acceptable salts thereof, are described as useful for the treatment of cognitive deficits associated with schizophrenia and other psychiatric, neurodegenerative and/or neurological disorders in mammals, including humans.

  公式I的化合物：其中X，Y，Z，R1，R2，R3，R4如此定义，并且其药学上可接受的盐，被描述为对哺乳动物，包括人类，治疗与精神分裂症和其他精神，神经退行性和/或神经系统疾病相关的认知缺陷有用。
• KAT II INHIBITORS
  申请人：Pfizer Inc.

  公开号：EP2646443B1

  公开（公告）日：2014-09-24
• US8598200B2
  申请人：——

  公开号：US8598200B2

  公开（公告）日：2013-12-03
• US8933095B2
  申请人：——

  公开号：US8933095B2

  公开（公告）日：2015-01-13