2-furan-2-yl-N⁵-pyrrolidin-2-ylmethyl-[1,2,4]triazolo[1,5-a][1,3,5]triazine-5,7-diamine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 2-furan-2-yl-N⁵-pyrrolidin-2-ylmethyl-[1,2,4]triazolo[1,5-a][1,3,5]triazine-5,7-diamine
• 化学式: C₁₃H₁₆N₈O
• 分子量: 300.323
• InChiKey: OBMONLOEBPIXGP-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.53
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  119.19
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2-furan-2-yl-N⁵-pyrrolidin-2-ylmethyl-[1,2,4]triazolo[1,5-a][1,3,5]triazine-5,7-diamine 、 5-氯-2-糠醛 在 溶剂黄146 、 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 为溶剂， 反应 18.5h， 生成 N⁵-[(R)-1-(5-Chloro-furan-2-ylmethyl)-pyrrolidin-2-ylmethyl]-2-furan-2-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazine-5,7-diamine
  参考文献：
  名称：

  Novel Diamino Derivatives of [1,2,4]Triazolo[1,5-a][1,3,5]triazine as Potent and Selective Adenosine A_2a Receptor Antagonists

  摘要：

  Piperazine derivatives of 2-furanyl[1,2,4]triazolo[1,5-a][1,3,5]triazine have recently been demonstrated to be potent and selective adenosine A(2a) receptor antagonists with oral activity in rodent models of Parkinson's disease. We have replaced the piperazinyl group with a variety of linear, monocyclic, and bicyclic diamines. Of these diamines, (R)-2-(aminomethyl)pyrrolidine is a particularly potent and selective replacement for the piperazinyl group. With this diamine component, we have been able to prepare numerous analogues with low nanomolar affinity toward the A(2a) receptor and good selectivity with respect to the A(1) receptor (> 200-fold in some cases). Selected analogues from this series of [1,2,4]triazolo[1,5-a][1,3,5]triazine have now been shown to be orally active in the mouse catalepsy model.

  DOI：

  10.1021/jm0498396
• 作为产物：
  描述：

  (R)-2-(氨甲基)-1-BOC-吡咯烷 在 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 6.0h， 生成 2-furan-2-yl-N⁵-pyrrolidin-2-ylmethyl-[1,2,4]triazolo[1,5-a][1,3,5]triazine-5,7-diamine
  参考文献：
  名称：

  Novel Diamino Derivatives of [1,2,4]Triazolo[1,5-a][1,3,5]triazine as Potent and Selective Adenosine A_2a Receptor Antagonists

  摘要：

  Piperazine derivatives of 2-furanyl[1,2,4]triazolo[1,5-a][1,3,5]triazine have recently been demonstrated to be potent and selective adenosine A(2a) receptor antagonists with oral activity in rodent models of Parkinson's disease. We have replaced the piperazinyl group with a variety of linear, monocyclic, and bicyclic diamines. Of these diamines, (R)-2-(aminomethyl)pyrrolidine is a particularly potent and selective replacement for the piperazinyl group. With this diamine component, we have been able to prepare numerous analogues with low nanomolar affinity toward the A(2a) receptor and good selectivity with respect to the A(1) receptor (> 200-fold in some cases). Selected analogues from this series of [1,2,4]triazolo[1,5-a][1,3,5]triazine have now been shown to be orally active in the mouse catalepsy model.

  DOI：

  10.1021/jm0498396

文献信息

• Novel Diamino Derivatives of [1,2,4]Triazolo[1,5-a][1,3,5]triazine as Potent and Selective Adenosine A_2a Receptor Antagonists
  作者：Chi B. Vu、Deborah Pan、Bo Peng、Gnanasambandam Kumaravel、Glenn Smits、Xiaowei Jin、Deepali Phadke、Thomas Engber、Carol Huang、Jennifer Reilly、Stacy Tam、Donna Grant、Gregg Hetu、Russell C. Petter

  DOI：10.1021/jm0498396

  日期：2005.3.1

  Piperazine derivatives of 2-furanyl[1,2,4]triazolo[1,5-a][1,3,5]triazine have recently been demonstrated to be potent and selective adenosine A(2a) receptor antagonists with oral activity in rodent models of Parkinson's disease. We have replaced the piperazinyl group with a variety of linear, monocyclic, and bicyclic diamines. Of these diamines, (R)-2-(aminomethyl)pyrrolidine is a particularly potent and selective replacement for the piperazinyl group. With this diamine component, we have been able to prepare numerous analogues with low nanomolar affinity toward the A(2a) receptor and good selectivity with respect to the A(1) receptor (> 200-fold in some cases). Selected analogues from this series of [1,2,4]triazolo[1,5-a][1,3,5]triazine have now been shown to be orally active in the mouse catalepsy model.