N7-{2-[4-(2,4-difluoro-phenyl)-piperazin-1-yl]-ethyl}-2-furan-2-yl-N7-methyl-[1,2,4]triazolo[1,5-c]pyrimidine-5,7-diamine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: N7-{2-[4-(2,4-difluoro-phenyl)-piperazin-1-yl]-ethyl}-2-furan-2-yl-N7-methyl-[1,2,4]triazolo[1,5-c]pyrimidine-5,7-diamine
• 英文别名: N7-(2-(4-(2,4-difluorophenyl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-N7-methyl-[1,2,4]triazolo[1,5-c]pyrimidine-5,7-diamine；7-N-[2-[4-(2,4-difluorophenyl)piperazin-1-yl]ethyl]-2-(furan-2-yl)-7-N-methyl-[1,2,4]triazolo[1,5-c]pyrimidine-5,7-diamine
• 化学式: C₂₂H₂₄F₂N₈O
• 分子量: 454.482
• InChiKey: AYDUITGMILRLFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  92
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  7-氯-2-呋喃-2-基[1,2,4]噻唑并[1,5-c]嘧啶-5-胺 在 三乙酰氧基硼氢化钠 、 cesium fluoride 、 三氟乙酸 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 N7-{2-[4-(2,4-difluoro-phenyl)-piperazin-1-yl]-ethyl}-2-furan-2-yl-N7-methyl-[1,2,4]triazolo[1,5-c]pyrimidine-5,7-diamine
  参考文献：
  名称：

  Triamino derivatives of triazolotriazine and triazolopyrimidine as adenosine A2a receptor antagonists

  摘要：

  Piperazine derivatives of 2-furanyl[1,2,4]triazolo[1,5-a][1,3,5]triazine have recently been shown to be potent and selective adenosine A(2a) receptor antagonists. We now demonstrate that potent and selective A(2a) receptor antagonists could still be obtained when the arylpiperazines are separated from the triazolotriazine core structure by an ethylenediamine spacer. Selected analogs bearing this triazolotriazine or the related triazolopyrimidine core structure have been found to be orally active in a mouse catalepsy model of Parkinson's disease. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.048

文献信息

• Potent and selective adenosine A2A receptor antagonists: 1,2,4-Triazolo[1,5-c]pyrimidines
  作者：Bernard R. Neustadt、Hong Liu、Jinsong Hao、William J. Greenlee、Andrew W. Stamford、Carolyn Foster、Leyla Arik、Jean Lachowicz、Hongtao Zhang、Rosalia Bertorelli、Silva Fredduzzi、Geoffrey Varty、Mary Cohen-Williams、Kwokei Ng

  DOI：10.1016/j.bmcl.2008.11.075

  日期：2009.2

  Antagonism of the adenosine A(2a) receptor offers great promise in the treatment of Parkinson's disease. In the course of exploring pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine A(2A) antagonists, which led to clinical candidate SCH 420814, we prepared 1,2,4-triazolo[1,5-c]pyrimidines with potent and selective (vs A(1)) A(2a) antagonist activity, including oral activity in the rat haloperidol-induced catalepsy model. Structure-activity relationships and plasma levels are described for this series. (C) 2008 Elsevier Ltd. All rights reserved.
• EP1618109A2
  申请人：——

  公开号：EP1618109A2

  公开（公告）日：2006-01-25
• [EN] TRIAZOLO[1,5-C]PYRIMIDINES & PYRAZOLO[1,5-C]PYRIMIDINES AND METHODS OF MAKING AND USING THE SAME<br/>[FR] TRIAZOLO[1,5-C]PYRIMIDINES ET PYRAZOLO[1,5-C]PYRIMIDINES ET PROCEDES DE PREPARATION ET D'UTILISATION DE CELLES-CI
  申请人：BIOGEN IDEC INC

  公开号：WO2004092172A2

  公开（公告）日：2004-10-28

  The invention is based on the discovery that compounds of formula (I) possess unexpectedly high affinity for the A2a adenosine receptor, and can be useful as antagonists thereof for preventing and/or treating numerous diseases, including Parkinson's disease. In one embodiment, the invention features a compound of formula (I) .
• Triamino derivatives of triazolotriazine and triazolopyrimidine as adenosine A2a receptor antagonists
  作者：Chi B. Vu、Pamela Shields、Bo Peng、Gnanasambandam Kumaravel、Xiaowei Jin、Deepali Phadke、Joy Wang、Thomas Engber、Eman Ayyub、Russell C. Petter

  DOI：10.1016/j.bmcl.2004.07.048

  日期：2004.10

  Piperazine derivatives of 2-furanyl[1,2,4]triazolo[1,5-a][1,3,5]triazine have recently been shown to be potent and selective adenosine A(2a) receptor antagonists. We now demonstrate that potent and selective A(2a) receptor antagonists could still be obtained when the arylpiperazines are separated from the triazolotriazine core structure by an ethylenediamine spacer. Selected analogs bearing this triazolotriazine or the related triazolopyrimidine core structure have been found to be orally active in a mouse catalepsy model of Parkinson's disease. (C) 2004 Elsevier Ltd. All rights reserved.