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2-(4-Methoxy-phenyl)-2H,5H-[1,2,4]triazolo[4,3-a]quinoxaline-1,4-dione | 204511-87-5

中文名称
——
中文别名
——
英文名称
2-(4-Methoxy-phenyl)-2H,5H-[1,2,4]triazolo[4,3-a]quinoxaline-1,4-dione
英文别名
2-(4-methoxyphenyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline-1,4-dione
2-(4-Methoxy-phenyl)-2H,5H-[1,2,4]triazolo[4,3-a]quinoxaline-1,4-dione化学式
CAS
204511-87-5
化学式
C16H12N4O3
mdl
——
分子量
308.296
InChiKey
MGIDLYMCJUPDJL-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    2
  • 重原子数:
    23
  • 可旋转键数:
    2
  • 环数:
    4.0
  • sp3杂化的碳原子比例:
    0.06
  • 拓扑面积:
    74.2
  • 氢给体数:
    1
  • 氢受体数:
    4

上下游信息

  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    参考文献:
    名称:
    1,2,4-Triazolo[4,3-a]quinoxalin-1-one Moiety as an Attractive Scaffold To Develop New Potent and Selective Human A3 Adenosine Receptor Antagonists:  Synthesis, Pharmacological, and Ligand−Receptor Modeling Studies
    摘要:
    In the past few years much effort in our laboratory has been directed toward the study of adenosine receptor antagonists, and recently we focused our attention on 2-aryl-1,2,4-triazolo[4,3-a]quinoxaline-1,4-diones and 2-aryl-1,2,4-triazolo [4,3-a]quinoxalin-4-amino-1-ones, some of which were potent and/or selective A(3) receptor antagonists. In the present paper, a new series of triazoloquinoxaline derivatives is described. Most of the new compounds, biologically evaluated in radioligand binding assays at bovine (b) A(1) and A(2A) and at human (h) A(1) and A(3) adenosine receptors, showed high hA(3) adenosine receptor affinity and selectivity. In particular, 2-(4-nitrophenyl)-1,2,4,5-tetrahydro-1,2,4-triazolo[4,3-a]quinoxaline-1,4-dione (1), also tested at the hA(2A) ARs, shows the best binding profile with a high hA(3) affinity (K-i = 0.60 nM) and strong selectivity vs hA(1) and vs hA(2A) receptors (both selectivity ratios greater than 16 600). To interpret our experimental results, we decided to theoretically depict the putative transmembrane binding motif of our triazoloquinoxaline analogues on hA(3) receptor. Structure-activity relationships have been explained analyzing the three-dimensional structure of the antagonist-receptor models obtained by molecular docking simulation.
    DOI:
    10.1021/jm031136l
  • 作为产物:
    参考文献:
    名称:
    三环杂芳环系统。1,2,4-Triazolo [4,3-a] 喹喔啉和 1,2,4-Triazino [4,3-a] 喹喔啉:合成和中枢苯二氮卓受体活性
    摘要:
    制备了一些 1,2,4-三唑并 [4,3-a] 喹喔啉 1-10 和 1,2,4-三嗪并 [4,3-a] 喹喔啉 11-12,并对其在苯二氮卓的结合进行了生物学评估大鼠皮层膜中的受体 (BZR)。BZR 亲和力为 1-10,表明 1 位质子受体的存在对 BZR 配体的效力很重要。另一方面,1,2,5-三酮衍生物 11-12 的 BZR 无活性表明基本 L2 亲脂取代基的正确搭配对于受体 - 配体相互作用至关重要。
    DOI:
    10.1002/ardp.19973301206
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