2-(4-Nitro-phenyl)-2H,5H-[1,2,4]triazolo[4,3-a]quinoxaline-1,4-dione | 204511-89-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-Nitro-phenyl)-2H,5H-[1,2,4]triazolo[4,3-a]quinoxaline-1,4-dione
• 英文别名: 2-(4-nitrophenyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline-1,4-dione
• CAS: 204511-89-7
• 化学式: C₁₅H₉N₅O₄
• 分子量: 323.268
• InChiKey: WUITWLXZVHPCHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(4-Nitro-phenyl)-2H,5H-[1,2,4]triazolo[4,3-a]quinoxaline-1,4-dione 在 palladium on activated charcoal 氢气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以62%的产率得到2-(4-Amino-phenyl)-2H,5H-[1,2,4]triazolo[4,3-a]quinoxaline-1,4-dione
  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
• 作为产物：
  描述：

  chloro-(4-nitro-phenylhydrazono)-acetic acid ethyl ester 在 三乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 8.0h， 生成 2-(4-Nitro-phenyl)-2H,5H-[1,2,4]triazolo[4,3-a]quinoxaline-1,4-dione
  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

文献信息

• 1,2,4-Triazolo[4,3-<i>a</i>]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
  作者：Vittoria Colotta、Daniela Catarzi、Flavia Varano、Francesca Romana Calabri、Ombretta Lenzi、Guido Filacchioni、Claudia Martini、Letizia Trincavelli、Francesca Deflorian、Stefano Moro

  DOI：10.1021/jm031136l

  日期：2004.7.1

  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.
• [EN] ADENOSINE RECEPTOR AGONISTS FOR THE TREATMENT AND PREVENTION OF VASCULAR OR JOINT CAPSULE CALCIFICATION DISORDERS<br/>[FR] AGONISTES DE RÉCEPTEUR D'ADÉNOSINE POUR LE TRAITEMENT ET LA PRÉVENTION DE TROUBLES DE CALCIFICATION DE CAPSULE VASCULAIRE OU ARTICULAIRE
  申请人：US HEALTH

  公开号：WO2011123518A1

  公开（公告）日：2011-10-06

  Disclosed are a method of treating or preventing a disorder in a mammal comprising administering to the mammal an adenosine receptor agonist or an adenosine receptor antagonist, either alone or in combination, in an amount effective to treat or prevent medial vascular or joint capsule calcification. Disclosed are methods of detecting or diagnosing a vascular or joint capsule calcification disorder, as well as a nucleic acid comprising a mutation in one or more exons of human NT5E selected from the group consisting of Exon 3, Exon 5, and Exon 9.