2-(furan-2-yl)-5-phenethoxy-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-amin | 139179-64-9

• 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)-5-phenethoxy-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-amin
• 英文别名: 2-(Furan-2-yl)-5-(2-phenylethoxy)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-amine
• CAS: 139179-64-9
• 化学式: C₁₆H₁₄N₆O₂
• 分子量: 322.326
• InChiKey: HWCWCJCMDSZBPJ-UHFFFAOYSA-N

物化性质

• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-呋喃甲酰肼 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 间氯过氧苯甲酸 、 sodium hydroxide 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， -5.0~170.0 ℃ 、600.01 kPa 条件下， 反应 49.0h， 生成 2-(furan-2-yl)-5-phenethoxy-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-amin
  参考文献：
  名称：

  Novel adenosine A2A receptor ligands: A synthetic, functional and computational investigation of selected literature adenosine A2A receptor antagonists for extending into extracellular space

  摘要：

  Growing evidence has suggested a role in targeting the adenosine A(2A) receptor for the treatment of Parkinson's disease. The literature compounds KW 6002 (2) and ZM 241385 (5) were used as a starting point from which a series of novel ligands targeting the adenosine A(2A) receptor were synthesized and tested in a recombinant human adenosine A(2A) receptor functional assay. In order to further explore these molecules, we investigated the biological effects of assorted linkers attached to different positions on selected adenosine A(2A) receptor antagonists, and assessed their potential binding modes using molecular docking studies. The results suggest that linking from the phenolic oxygen of selected adenosine A(2A) receptor antagonists is relatively well tolerated due to the extension towards extracellular space, and leads to the potential of attaching further functionality from this position. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.070

文献信息

• Azole Derivatives
  申请人：ZENECA LIMITED

  公开号：EP0459702A1

  公开（公告）日：1991-12-04

  The invention concerns novel, pharmaceutically useful compounds of formula I in which Q is a 5-membered heteroaryl optionally bearing 1 or 2 substituents independently selected from (1-4C)alkyl and halogeno ; R1 is hydrogen, (1-6C)alkyl, or (1-4C)alkanoyl ; R2 (when not as hereinbelow defined together with X) is hydrogen, (3-12C)cycloalkyl, (3-6C)alkenyl, phenyl(3-6C)alkenyl, tetrafluorophenyl, pentafluorophenyl, 5- or 6-membered heteroaryl, optionally substituted (1-6C)alkyl or optionally substituted phenyl ; X is oxy, thio, sulphinyl, sulphonyl or an imino group of formula -NRa- in which Ra is hydrogen, (1-6C)alkyl or together with R2 and the adjacent nitrogen atom forms a 4 to 6-membered saturated heterocyclic ring ; and A is N or CT in which T is hydrogen or (1-4C)alkyl ; or a pharmaceutically acceptable salt thereof ; processes for the manufacture of the compounds and pharmaceutical compositions containing them. The compounds are useful as adenosine antagonists. The invention further provides novel intermediates useful in the manufacture of the compounds of formula I.

  本发明涉及式 I 的新型药用化合物，其中 Q 是 5 元杂芳基，任选带有 1 或 2 个独立选自 (1-4C)烷基和卤素的取代基；R1 是氢、(1-6C)烷基或 (1-4C)alkanoyl ；R2（当不与 X 一起定义时）是氢、(3-12C)环烷基、(3-6C)烯基、苯基(3-6C)烯基、四氟苯基、五氟苯基、5 或 6 元杂芳基、任选取代的(1-6C)烷基或任选取代的苯基；X 是氧、硫代、亚砜基、磺酰基或式 -NRa- 的亚氨基，其中 Ra 是氢、(1-6C)烷基或与 R2 和邻近的氮原子一起形成 4 至 6 元饱和杂环；以及 A 是 N 或 CT，其中 T 是氢或 (1-4C)烷基；或其药学上可接受的盐；化合物的制造工艺和含有这些化合物的药物组合物。这些化合物可用作腺苷拮抗剂。本发明进一步提供了用于制造式 I 化合物的新型中间体。
• US5270311A
  申请人：——

  公开号：US5270311A

  公开（公告）日：1993-12-14
• US5356894A
  申请人：——

  公开号：US5356894A

  公开（公告）日：1994-10-18
• Novel adenosine A2A receptor ligands: A synthetic, functional and computational investigation of selected literature adenosine A2A receptor antagonists for extending into extracellular space
  作者：Manuela Jörg、Jeremy Shonberg、Frankie S. Mak、Neil D. Miller、Elizabeth Yuriev、Peter J. Scammells、Ben Capuano

  DOI：10.1016/j.bmcl.2013.03.070

  日期：2013.6

  Growing evidence has suggested a role in targeting the adenosine A(2A) receptor for the treatment of Parkinson's disease. The literature compounds KW 6002 (2) and ZM 241385 (5) were used as a starting point from which a series of novel ligands targeting the adenosine A(2A) receptor were synthesized and tested in a recombinant human adenosine A(2A) receptor functional assay. In order to further explore these molecules, we investigated the biological effects of assorted linkers attached to different positions on selected adenosine A(2A) receptor antagonists, and assessed their potential binding modes using molecular docking studies. The results suggest that linking from the phenolic oxygen of selected adenosine A(2A) receptor antagonists is relatively well tolerated due to the extension towards extracellular space, and leads to the potential of attaching further functionality from this position. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.