3-benzyl-8-bromo-7-(2-oxopropyl)-1-propyl-3,7-dihydropurine-2,6-dione | 862468-81-3

• 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-8-bromo-7-(2-oxopropyl)-1-propyl-3,7-dihydropurine-2,6-dione
• 英文别名: 3-benzyl-8-bromo-7-(2-oxobutyl)-1-propyl-3,7-dihydropurine-2,6-dione；3-BENZYL-8-BROMO-7-(2-OXO-PROPYL)-1-PROPYL-3,7-DIHYDRO-PURINE-2,6-DIONE；3-Benzyl-8-bromo-7-(2-oxopropyl)-1-propylpurine-2,6-dione
• CAS: 862468-81-3
• 化学式: C₁₈H₁₉BrN₄O₃
• 分子量: 419.278
• InChiKey: KIRMMMFGVDSUET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  75.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-benzyl-8-bromo-7-(2-oxopropyl)-1-propyl-3,7-dihydropurine-2,6-dione 在 氨 作用下， 以 乙醇 为溶剂， 以90%的产率得到1-benzyl-7-methyl-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：

  一氯丙酮 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 生成 3-benzyl-8-bromo-7-(2-oxopropyl)-1-propyl-3,7-dihydropurine-2,6-dione
  参考文献：
  名称：

  Novel adenosine A3 receptor modulators

  摘要：

  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。

  公开号：

  US20060178385A1

文献信息

• Structure–activity relationship studies of a new series of imidazo[2,1-f]purinones as potent and selective A3 adenosine receptor antagonists
  作者：Pier Giovanni Baraldi、Delia Preti、Mojgan Aghazadeh Tabrizi、Romeo Romagnoli、Giulia Saponaro、Stefania Baraldi、Maurizio Botta、Cesare Bernardini、Andrea Tafi、Tiziano Tuccinardi

  DOI：10.1016/j.bmc.2008.10.049

  日期：2008.12.15

  We recently described the synthesis of 1-benzyl-3-propyl-1H,8H-imidazo[2,1-f]purine-2,4-diones, new potent and selective A(3) adenosine receptor antagonists containing a xanthine core. The present work can be considered an extension of our SAR studies on related structures in which the effect of different kind of substitutions at the 1-, 3- and 8-positions has been evaluated in order to improve both the potency and the hydrophilicity of the originally synthesised molecules. The A(3) binding disposition of these compounds was also investigated through docking and 3D-QSAR studies. (C) 2008 Elsevier Ltd. All rights reserved.
• US7435740B2
  申请人：——

  公开号：US7435740B2

  公开（公告）日：2008-10-14
• 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。
• New Pyrrolo[2,1-<i>f</i>]purine-2,4-dione and Imidazo[2,1-<i>f</i>]purine-2,4-dione Derivatives as Potent and Selective Human A₃ Adenosine Receptor Antagonists
  作者：Pier Giovanni Baraldi、Delia Preti、Mojgan Aghazadeh Tabrizi、Francesca Fruttarolo、Romeo Romagnoli、Naser Abdel Zaid、Allan R. Moorman、Stefania Merighi、Katia Varani、Pier Andrea Borea

  DOI：10.1021/jm058008c

  日期：2005.7.1

  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.