ST 1680

• 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: ST 1680
• 英文别名: 1-Methyl-2-(triazol-2-yl)imidazo[4,5-c]pyridin-4-amine;trifluoromethanesulfonic acid
• 化学式: CHF₃O₃S*C₉H₉N₇
• 分子量: 365.296
• InChiKey: AVRNFQKHOOMRFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.53
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  150
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2-氯-N4-甲基嘧啶-3,4-二胺 在 盐酸 、 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.0h， 生成 ST 1680
  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

文献信息

• 2-<i>n</i>-Butyl-9-methyl-8-[1,2,3]triazol-2-yl-9<i>H</i>-purin-6-ylamine and Analogues as A_2A Adenosine Receptor Antagonists. Design, Synthesis, and Pharmacological Characterization
  作者：Patrizia Minetti、Maria Ornella Tinti、Paolo Carminati、Massimo Castorina、Maria Assunta Di Cesare、Stefano Di Serio、Grazia Gallo、Orlando Ghirardi、Fabrizio Giorgi、Luca Giorgi、Giovanni Piersanti、Francesca Bartoccini、Giorgio Tarzia

  DOI：10.1021/jm058018d

  日期：2005.11.1

  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.