2-环戊基-1H-咪唑并[4,5-b]吡啶 | 119628-83-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 中文名称: 2-环戊基-1H-咪唑并[4,5-b]吡啶
• 英文名称: 2-Cyclopentyl-1H-imidazo[4,5-B]pyridine
• CAS: 119628-83-0
• 化学式: C₁₁H₁₃N₃
• 分子量: 187.244
• InChiKey: DHCJZAGWHJCYOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-环戊基-1H-咪唑并[4,5-b]吡啶 在 palladium dihydroxide 、 四(三苯基膦)钯 双氧水 、 硝酸 、 ammonium formate 、 potassium carbonate 、 溶剂黄146 、 三氟乙酸 、 三氯氧磷 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 20.0~150.0 ℃ 、1.8 MPa 条件下， 反应 70.91h， 生成 LUF5816
  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：

  2,3-二氨基吡啶 、 环戊酸 在 PPA 作用下， 反应 5.0h， 以10%的产率得到2-环戊基-1H-咪唑并[4,5-b]吡啶
  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

• OEZDEN, S., ANKARA UENIV. ESZACILIK FAK. MECMUASI, 1981, 11, N 1, 80-102
  作者：OEZDEN, S.

  DOI：——

  日期：——
• 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.