2,6-dichloro-9-benzyl-1-deazapurine | 500896-84-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 2,6-dichloro-9-benzyl-1-deazapurine
• 英文别名: 3-Benzyl-5,7-dichloro-3H-imidazo[4,5-b]pyridine；3-benzyl-5,7-dichloroimidazo[4,5-b]pyridine
• CAS: 500896-84-4
• 化学式: C₁₃H₉Cl₂N₃
• 分子量: 278.141
• InChiKey: JSDNILHZXAEKMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,6-dichloro-9-benzyl-1-deazapurine 在 palladium dihydroxide 、 四(三苯基膦)钯 ammonium formate 、 potassium carbonate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 0.83h， 生成 2,6-Diphenyl-1-deazapurine
  参考文献：
  名称：

  2,6,8-Trisubstituted 1-Deazapurines as Adenosine Receptor Antagonists

  摘要：

  In this study we developed a refined pharmacophore model for antagonists of the human adenosine A(1) receptor, based on features of known pyrimidine and purine derivatives. The adoption of these updated criteria assisted us in synthesizing a series of 1-deazapurines with consistently high affinity as inverse agonists for the adenosine A(1) receptor. These 1-deazapurines (otherwise known as 3H-imidazo[4,5-b]pyridines) were substituted at their 2- and 6-positions, yielding a series with five of the derivatives displaying K-i values in the subnanomolar range. The most potent of these, compound 10 (LUF 5978), displayed an affinity of 0.55 nM at the human adenosine A(1) receptor with > 300-fold and 45-fold selectivity toward A(2A) and A(3) receptors, respectively. Compound 14 (LUF 5981, K-i = 0.90 nM) appeared to have the best overall selectivity with respect to adenosine A(2A) (> 200-fold) and A(3) (700-fold) receptors.

  DOI：

  10.1021/jm0607956
• 作为产物：
  描述：

  4-hydroxy-7-nitroimidazo[4,5-b]pyridine 在 potassium carbonate 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.5h， 生成 2,6-dichloro-9-benzyl-1-deazapurine
  参考文献：
  名称：

  2,6,8-Trisubstituted 1-Deazapurines as Adenosine Receptor Antagonists

  摘要：

  In this study we developed a refined pharmacophore model for antagonists of the human adenosine A(1) receptor, based on features of known pyrimidine and purine derivatives. The adoption of these updated criteria assisted us in synthesizing a series of 1-deazapurines with consistently high affinity as inverse agonists for the adenosine A(1) receptor. These 1-deazapurines (otherwise known as 3H-imidazo[4,5-b]pyridines) were substituted at their 2- and 6-positions, yielding a series with five of the derivatives displaying K-i values in the subnanomolar range. The most potent of these, compound 10 (LUF 5978), displayed an affinity of 0.55 nM at the human adenosine A(1) receptor with > 300-fold and 45-fold selectivity toward A(2A) and A(3) receptors, respectively. Compound 14 (LUF 5981, K-i = 0.90 nM) appeared to have the best overall selectivity with respect to adenosine A(2A) (> 200-fold) and A(3) (700-fold) receptors.

  DOI：

  10.1021/jm0607956

文献信息

• 2,6,8-Trisubstituted 1-Deazapurines as Adenosine Receptor Antagonists
  作者：Lisa C. W. Chang、Jacobien K. von Frijtag Drabbe Künzel、Thea Mulder-Krieger、Joost Westerhout、Thomas Spangenberg、Johannes Brussee、Adriaan P. IJzerman

  DOI：10.1021/jm0607956

  日期：2007.2.1

  In this study we developed a refined pharmacophore model for antagonists of the human adenosine A(1) receptor, based on features of known pyrimidine and purine derivatives. The adoption of these updated criteria assisted us in synthesizing a series of 1-deazapurines with consistently high affinity as inverse agonists for the adenosine A(1) receptor. These 1-deazapurines (otherwise known as 3H-imidazo[4,5-b]pyridines) were substituted at their 2- and 6-positions, yielding a series with five of the derivatives displaying K-i values in the subnanomolar range. The most potent of these, compound 10 (LUF 5978), displayed an affinity of 0.55 nM at the human adenosine A(1) receptor with > 300-fold and 45-fold selectivity toward A(2A) and A(3) receptors, respectively. Compound 14 (LUF 5981, K-i = 0.90 nM) appeared to have the best overall selectivity with respect to adenosine A(2A) (> 200-fold) and A(3) (700-fold) receptors.