2-furan-2-yl-5-piperazin-1-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine | 735316-45-7

• 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: 2-furan-2-yl-5-piperazin-1-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine
• 英文别名: 2-(furan-2-yl)-5-piperazin-1-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-amine
• CAS: 735316-45-7
• 化学式: C₁₂H₁₄N₈O
• 分子量: 286.296
• InChiKey: JVGXNLGFJFMKDV-UHFFFAOYSA-N

物化性质

• 密度：
  1.78±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N,N'-二甲基乙二胺 、 2-furan-2-yl-5-piperazin-1-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine 以 乙腈 为溶剂， 反应 2.0h， 生成 2-furan-2-yl-N5-methyl-N5-(2-methylamino-ethyl)-[1,2,4]triazolo[1,5-a][1,3,5]triazine-5,7-diamine
  参考文献：
  名称：

  [EN] TRIAZOLOTRIAZINES AND PYRAZOLOTRIAZINES USEFUL AS A2A ADENOSINE RECEPTOR ANTAGON ISTS
  [FR] TRIAZOLOTRIAZINES ET PYRAZOLOTRIAZINES ET LEURS PROCEDES DE FABRICATION ET D'UTILISATION

  摘要：

  公开号：

  WO2004092170A3
• 作为产物：
  描述：

  7-氨基-2-(2-呋喃基)-5-甲基磺酰基-[1,2,4]噻唑并[1,5-a][1,3,5]三嗪 、 哌嗪 在 水 、 Brine 、 Sodium sulfate-III 、 crude product 、 二氯甲烷 、 甲醇 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以to afford 2-furan-2-yl-5-piperazin-1-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine的产率得到2-furan-2-yl-5-piperazin-1-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine
  参考文献：
  名称：

  Triazolotriazines and pyrazolotriazines and methods of making and using the same

  摘要：

  该发明基于发现，化合物(I)的公式具有意外的高亲和力，可用作拮抗剂，用于预防和/或治疗许多疾病，包括帕金森病的A2a腺苷受体。在一种实施例中，该发明涉及公式I的化合物：(I)。

  公开号：

  US20060276475A1

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.
• Piperazine Derivatives of [1,2,4]Triazolo[1,5-<i>a</i>][1,3,5]triazine as Potent and Selective Adenosine A₂_a Receptor Antagonists
  作者：Chi B. Vu、Bo Peng、Gnanasambandam Kumaravel、Glenn Smits、Xiaowei Jin、Deepali Phadke、Thomas Engber、Carol Huang、Jennifer Reilly、Stacy Tam、Donna Grant、Gregg Hetu、Liqing Chen、Jianbo Zhang、Russell C. Petter

  DOI：10.1021/jm0498405

  日期：2004.8.1

  The [1,2,4]triazolo[1,5-a]triazine derivative 3, more commonly known in the field of adenosine research as ZM-241385, has previously been demonstrated to be a potent and selective adenosine A(2a) receptor antagonist, although with limited oral bioavailability. This [1,2,4]triazolo[1,5-a]triazine core structure has now been improved by incorporating various piperazine derivatives. With some preliminary optimization, the A2a binding affinity of some of the best piperazine derivatives is almost as good as that of compound 3. The selectivity level over the adenosine A, receptor subtype for some of the more active analogues is also fairly high, >400-fold in some cases. Many compounds within this piperazine series of [1,2,4]triazolo[1,5-a]triazine have now been shown to have good oral bioavailability in the rat, with some as high as 89% (compound 35). More significantly, some piperazines derivatives of [1,2,4]triazolo[1,5-a]triazine also possessed good oral efficacy in rodent models of Parkinson's disease. For instance, compound 34 was orally active in the rat catalepsy model at 3 mg/kg. In the 6-hydroxydopamine-lesioned rat model, this compound was also quite effective, with a minimum effective dose of 3 mg/kg po.
• EP1615930A2
  申请人：——

  公开号：EP1615930A2

  公开（公告）日：2006-01-18
• US7285550B2
  申请人：——

  公开号：US7285550B2

  公开（公告）日：2007-10-23
• [EN] TRIAZOLOTRIAZINES AND PYRAZOLOTRIAZINES AND METHODS OF MAKING AND USING THE SAME<br/>[FR] TRIAZOLOTRIAZINES ET PYRAZOLOTRIAZINES ET LEURS PROCEDES DE FABRICATION ET D'UTILISATION
  申请人：BIOGEN IDEC INC

  公开号：WO2004092170A2

  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: (I)