dibenzyl-(8-bromo-9-methyl-2-n-pentyl-9H-purin-6-yl)amine | 496955-60-3

• 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: dibenzyl-(8-bromo-9-methyl-2-n-pentyl-9H-purin-6-yl)amine
• CAS: 496955-60-3
• 化学式: C₂₅H₂₈BrN₅
• 分子量: 478.435
• InChiKey: NSTXCERZJCBQSW-UHFFFAOYSA-N

物化性质

• 熔点：
  97 °C(Solv: dichloromethane (75-09-2))
• 沸点：
  560.5±60.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.07
• 重原子数：
  31.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  46.84
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  dibenzyl-(8-bromo-9-methyl-2-n-pentyl-9H-purin-6-yl)amine 在 三氟甲磺酸 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 ST 2097
  参考文献：
  名称：

  2-n-Butyl-9-methyl-8-[1,2,3]triazol-2-yl-9H-purin-6-ylamine and Analogues as A_2A Adenosine Receptor Antagonists. Design, Synthesis, and Pharmacological Characterization

  摘要：

  Two types of adenosine receptor ligands were designed, i.e., 9H-purine and 1H-imidazo[4,5-c]pyridines, to obtain selective A(2A) antagonists, and we report here their synthesis and binding affinities for the four adenosine receptor subtypes A(1), A(2A), A(2B) and A(3). The design was carried out on the basis of the molecular modeling of a number of potent adenosine receptor antagonists described in the literature. Three compounds (25b-d) showed an interesting affinity and selectivity for the A(2A) subtype. One of them, i.e., ST1535 (2-n-butyl-9-methyl-8-[1,2,3]triazol-2-yl-9H-purin-6-ylamine, 25b) (K-i A(2A) = 6.6 nM, K-i A(1)/A(2A) = 12; K-i A(2B)/A(2A) = 58; K-i A(3)/A(2A) > 160), was selected for in vivo study and shown to induce a dose-related increase in locomotor activity, suggestive of an A(2A) antagonist type of activity.

  DOI：

  10.1021/jm058018d
• 作为产物：
  描述：

  dibenzyl-(9-methyl-2-n-pentyl-9H-purin-6-yl)amine 在 溴 作用下， 以 四氢呋喃 、 甲醇 、 acetate buffer 为溶剂， 反应 12.0h， 以80%的产率得到dibenzyl-(8-bromo-9-methyl-2-n-pentyl-9H-purin-6-yl)amine
  参考文献：
  名称：

  2-n-Butyl-9-methyl-8-[1,2,3]triazol-2-yl-9H-purin-6-ylamine and Analogues as A_2A Adenosine Receptor Antagonists. Design, Synthesis, and Pharmacological Characterization

  摘要：

  Two types of adenosine receptor ligands were designed, i.e., 9H-purine and 1H-imidazo[4,5-c]pyridines, to obtain selective A(2A) antagonists, and we report here their synthesis and binding affinities for the four adenosine receptor subtypes A(1), A(2A), A(2B) and A(3). The design was carried out on the basis of the molecular modeling of a number of potent adenosine receptor antagonists described in the literature. Three compounds (25b-d) showed an interesting affinity and selectivity for the A(2A) subtype. One of them, i.e., ST1535 (2-n-butyl-9-methyl-8-[1,2,3]triazol-2-yl-9H-purin-6-ylamine, 25b) (K-i A(2A) = 6.6 nM, K-i A(1)/A(2A) = 12; K-i A(2B)/A(2A) = 58; K-i A(3)/A(2A) > 160), was selected for in vivo study and shown to induce a dose-related increase in locomotor activity, suggestive of an A(2A) antagonist type of activity.

  DOI：

  10.1021/jm058018d