4-(8-amino-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-benzoic acid | 785050-87-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并吡嗪类
• 英文名称: 4-(8-amino-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-benzoic acid
• 英文别名: 4-[8-amino-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]benzoic acid
• CAS: 785050-87-5
• 化学式: C₁₆H₁₁N₅O₃
• 分子量: 321.295
• InChiKey: BDZIPBIZHWIAQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-(8-amino-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-benzoic acid 、 1-(3-氨基丙基)咪唑 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-(8-amino-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-N-(3-imidazol-1-yl-propyl)-benzamide
  参考文献：
  名称：

  Synthesis of [1,2,4]triazolo[1,5-a]pyrazines as adenosine A2A receptor antagonists

  摘要：

  Potent and selective antagonists of the adenosine A(2A) receptor often contain a nitrogen-rich fused-ring heterocyclic core. Replacement of the core with an isomeric ring system has previously been shown to improve target affinity, selectivity, and in vivo activity. This paper describes the preparation, by a novel route, of A(2A) receptor antagonists containing the [1,2,4]triazolo[1,5-a]pyrazine nucleus, which is isomeric with the [1,2,4]triazolo[1,5-c]pyrimidine core of a series of known A(2A) antagonists with in vivo activity in animal models of Parkinson's disease. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.052

文献信息

• [EN] TRIAZOLOPYRAZINES AND METHODS OF MAKING AND USING THE SAME<br/>[FR] TRIAZOLOPYRAZINES ET PROCEDES DE PREPARATION ET D'UTILISATION CE CELLES-CI
  申请人：BIOGEN IDEC INC

  公开号：WO2004092177A1

  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 (See formula on paper copy)

  这项发明基于发现，式(I)化合物具有对A2a腺苷受体具有意外高亲和力，并可用作其拮抗剂，用于预防和/或治疗包括帕金森病在内的多种疾病。在一个实施例中，该发明涉及一种式I的化合物（请参见纸质副本上的式）。
• Triazolopyrazines and methods of making and using the same
  申请人：Dowling E James

  公开号：US20070010520A1

  公开（公告）日：2007-01-11

  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 (See formula on paper copy)

  该发明基于发现，式(I)化合物具有意外的高亲和力，可作为A2a腺苷受体的拮抗剂，用于预防和/或治疗包括帕金森病在内的许多疾病。在一种实施方式中，该发明涉及式(I)化合物（见纸质复印件上的式子）。
• EP1615931A1
  申请人：——

  公开号：EP1615931A1

  公开（公告）日：2006-01-18
• Synthesis of [1,2,4]triazolo[1,5-a]pyrazines as adenosine A2A receptor antagonists
  作者：James E. Dowling、Jeffrey T. Vessels、Serajul Haque、He Xi Chang、Kurt van Vloten、Gnanasambandam Kumaravel、Thomas Engber、Xiaowei Jin、Deepali Phadke、Joy Wang、Eman Ayyub、Russell C. Petter

  DOI：10.1016/j.bmcl.2005.07.052

  日期：2005.11

  Potent and selective antagonists of the adenosine A(2A) receptor often contain a nitrogen-rich fused-ring heterocyclic core. Replacement of the core with an isomeric ring system has previously been shown to improve target affinity, selectivity, and in vivo activity. This paper describes the preparation, by a novel route, of A(2A) receptor antagonists containing the [1,2,4]triazolo[1,5-a]pyrazine nucleus, which is isomeric with the [1,2,4]triazolo[1,5-c]pyrimidine core of a series of known A(2A) antagonists with in vivo activity in animal models of Parkinson's disease. (c) 2005 Elsevier Ltd. All rights reserved.