3-benzyl-1-propyl-3,7-dihydropurine-2,6-dione | 862468-65-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 3-benzyl-1-propyl-3,7-dihydropurine-2,6-dione
• 英文别名: 1-PROPYL-3-BENZYL-XANTHINE；1-Propyl-3-benzyl xanthine；3-benzyl-1-propyl-7H-purine-2,6-dione
• CAS: 862468-65-3
• 化学式: C₁₅H₁₆N₄O₂
• 分子量: 284.318
• InChiKey: HWLZWMZDBLPNOK-UHFFFAOYSA-N

物化性质

• 熔点：
  200-202 °C(Solv: ethanol (64-17-5))
• 沸点：
  545.1±52.0 °C(Predicted)
• 密度：
  1.320±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  69.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-benzyl-1-propyl-3,7-dihydropurine-2,6-dione 在 氨 、 溴 、 sodium acetate 、 potassium carbonate 、 溶剂黄146 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.08h， 生成 1-benzyl-6,7-dimethyl-3-propyl-1H-imidazo[1,2-f]purine-2,4(3H,8H)-dione
  参考文献：
  名称：

  New Pyrrolo[2,1-f]purine-2,4-dione and Imidazo[2,1-f]purine-2,4-dione Derivatives as Potent and Selective Human A₃ Adenosine Receptor Antagonists

  摘要：

  Compounds presenting an additional fused ring on the xanthine nucleus have been reported to exhibit antagonistic activity with various levels of affinity and selectivity toward the four adenosine receptors subtypes A(1) A(2A), A(2B), and A(3). This paper reports synthesis and biological evaluation of new 1-benzyl-3-propyl-IH,6H-pyrrolo[2,1-f]purine-2,4-diones and 1-benzyl-3propyl- 1H,8H-imidazo [2, 1-f] purine-2,4-diones, among which we identified potent and selective A(3) adenosine receptors antagonists. In particular, 1-benzyl-7-methyl-3-propyl-IH,8H-imidazo[2,1-f]purine-2,4-dione (11e) shows a K-i (hA(3)) value from binding assay of 0.8 nM.

  DOI：

  10.1021/jm058008c
• 作为产物：
  描述：

  6-amino-1-benzyl-5-nitroso-3-propylpyrimidine-2,4(1H,3H)-dione 在 sodium dithionite 作用下， 反应 2.5h， 生成 3-benzyl-1-propyl-3,7-dihydropurine-2,6-dione
  参考文献：
  名称：

  New Pyrrolo[2,1-f]purine-2,4-dione and Imidazo[2,1-f]purine-2,4-dione Derivatives as Potent and Selective Human A₃ Adenosine Receptor Antagonists

  摘要：

  Compounds presenting an additional fused ring on the xanthine nucleus have been reported to exhibit antagonistic activity with various levels of affinity and selectivity toward the four adenosine receptors subtypes A(1) A(2A), A(2B), and A(3). This paper reports synthesis and biological evaluation of new 1-benzyl-3-propyl-IH,6H-pyrrolo[2,1-f]purine-2,4-diones and 1-benzyl-3propyl- 1H,8H-imidazo [2, 1-f] purine-2,4-diones, among which we identified potent and selective A(3) adenosine receptors antagonists. In particular, 1-benzyl-7-methyl-3-propyl-IH,8H-imidazo[2,1-f]purine-2,4-dione (11e) shows a K-i (hA(3)) value from binding assay of 0.8 nM.

  DOI：

  10.1021/jm058008c

文献信息

• Novel adenosine A3 receptor modulators
  申请人：Baraldi Giovanni Pier

  公开号：US20060178385A1

  公开（公告）日：2006-08-10

  A class of novel antagonists for the adenosine A 3 receptor are disclosed. These compounds are useful as therapeutic agents for a number of diseases and medical conditions that are mediated by the A 3 receptor. The compounds of this invention are also useful as diagnostic agents for the A 3 receptor.

  本发明揭示了一类新型的腺苷A3受体拮抗剂。这些化合物可用作治疗多种由A3受体介导的疾病和医疗状况的治疗剂。本发明的这些化合物还可用作A3受体的诊断试剂。
• Adenosine A3 receptor modulators
  申请人：King Pharmaceuticals Research and Development, Inc.

  公开号：US07435740B2

  公开（公告）日：2008-10-14

  A class of novel antagonists for the adenosine A3 receptor are disclosed. These compounds are useful as therapeutic agents for a number of diseases and medical conditions that are mediated by the A3 receptor. The compounds of this invention are also useful as diagnostic agents for the A3 receptor.

  本发明揭示了一类新型的腺苷A3受体拮抗剂。这些化合物可用作治疗许多由A3受体介导的疾病和医疗状况的治疗剂。本发明的化合物也可用作A3受体的诊断剂。
• NOVEL ADENOSINE A3 RECEPTOR MODULATORS
  申请人：King Pharmaceuticals Research and Development Inc.

  公开号：EP1845993A2

  公开（公告）日：2007-10-24
• EP1845993A4
  申请人：——

  公开号：EP1845993A4

  公开（公告）日：2009-03-11
• US7435740B2
  申请人：——

  公开号：US7435740B2

  公开（公告）日：2008-10-14