3-benzyl-8-bromo-7-(2-cyclohexyl-2-oxoethyl)-1-propyl-3,7-dihydropurine-2,6-dione | 862468-86-8

• 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-cyclohexyl-2-oxoethyl)-1-propyl-3,7-dihydropurine-2,6-dione
• 英文别名: 3-Benzyl-8-bromo-7-(2-cyclohexyl-2-oxoethyl)-1-propylpurine-2,6-dione
• CAS: 862468-86-8
• 化学式: C₂₃H₂₇BrN₄O₃
• 分子量: 487.396
• InChiKey: MIACIBSEDVSPJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 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-cyclohexyl-2-oxoethyl)-1-propyl-3,7-dihydropurine-2,6-dione 在 氨 作用下， 以 乙醇 为溶剂， 以40%的产率得到1-benzyl-7-cyclohexyl-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：

  3-benzyl-1-propyl-3,7-dihydropurine-2,6-dione 在 溴 、 sodium acetate 、 potassium carbonate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.08h， 生成 3-benzyl-8-bromo-7-(2-cyclohexyl-2-oxoethyl)-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

• 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.