1-benzyl-5-methyl-4,6-dioxo-4,5,6,7-tetrahydropyrazolo<3,4-d>pyrimidine | 106273-67-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并嘧啶类
• 英文名称: 1-benzyl-5-methyl-4,6-dioxo-4,5,6,7-tetrahydropyrazolo<3,4-d>pyrimidine
• 英文别名: 1-benzyl-5-methyl-1,7-dihydro-pyrazolo[3,4-d]pyrimidine-4,6-dione；1-Benzyl-5-methyl-1,7-dihydro-pyrazolo[3,4-d]pyrimidin-4,6-dion；1-benzyl-5-methyl-7H-pyrazolo[3,4-d]pyrimidine-4,6-dione
• CAS: 106273-67-0
• 化学式: C₁₃H₁₂N₄O₂
• 分子量: 256.264
• InChiKey: RZOAOIWZRJHYGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  67.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-benzyl-5-methyl-4,6-dioxo-4,5,6,7-tetrahydropyrazolo<3,4-d>pyrimidine 在 三氯氧磷 作用下， 反应 48.0h， 以67%的产率得到1-Benzyl-6-chloro-5-methylpyrazolo[3,4-d]pyrimidin-4-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：

  5-氨基-1-苄基吡唑-4-甲酰胺 在 sodium hydroxide 作用下， 生成 1-benzyl-5-methyl-4,6-dioxo-4,5,6,7-tetrahydropyrazolo<3,4-d>pyrimidine
  参考文献：
  名称：

  杂环系列中的药用化学研究。第25次通讯。吡唑并[3,4-d]嘧啶系列的吡唑并嘧啶III对黄嘌呤，可可碱和茶碱类似物† ‡ §

  摘要：

  对黄嘌呤，可可碱和茶碱异构体1，5-的制备；2.5和1.7；描述了2,7-和5,7-二甲基-4,6-二氧代-4,5,6,7-四氢-吡唑并[3,4-d]-嘧啶并确定了它们的结构。咖啡因和异咖啡因异构体1,5,7-和2,5,7-三甲基-4,6-二氧代-4,5,6,7-四氢吡唑并[3,4-d]嘧啶的结构特异性合成实现。

  DOI：

  10.1002/hlca.19590420132

文献信息

• Avasthi; Chandra; Rawat, Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1998, vol. 37, # 12, p. 1228 - 1233
  作者：Avasthi、Chandra、Rawat、Bhakuni

  DOI：——

  日期：——