2-(3-Fluoro-phenyl)-2H,5H-[1,2,4]triazolo[4,3-a]quinoxaline-1,4-dione | 204511-81-9

• 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-(3-Fluoro-phenyl)-2H,5H-[1,2,4]triazolo[4,3-a]quinoxaline-1,4-dione
• 英文别名: 2-(3-fluorophenyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline-1,4-dione
• CAS: 204511-81-9
• 化学式: C₁₅H₉FN₄O₂
• 分子量: 296.26
• InChiKey: WCKOWZHGRPXWIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 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：
  65
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3-Fluoro-phenyl)-2H,5H-[1,2,4]triazolo[4,3-a]quinoxaline-1,4-dione 在 吡啶 、 五氯化磷 、 三乙胺 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 生成 4-Cyclohexylamino-2-(3-fluoro-phenyl)-2H-[1,2,4]triazolo[4,3-a]quinoxalin-1-one
  参考文献：
  名称：

  1,2,4-Triazolo[4,3-a]quinoxalin-1-one:  A Versatile Tool for the Synthesis of Potent and Selective Adenosine Receptor Antagonists

  摘要：

  4-Amino-6-benzylamino-1,2-dihydro-2-phenyl-1,2,4-triazolo[4,3-a]quinoxalin-1-one (1) has been found to be an A(2A) versus A(1) selective antagonist (Colotta et al. Arch. Pharm. Pharm. Med. Chem. 1999,332, 39-41). In this paper some novel triazoloquinoxalin-1-ones 4-25 bearing different substituents on the 2-phenyl and/or 4-amino moiety of the parent 4-amino-1,2-dihydro-2-phenyl-1,2,4-triazolo[4,3-a]quinoxalin-1-one (3) have been synthesized and tested in radioligand binding assays at bovine A(1) and A(2A) and cloned human A(3) adenosine receptors (AR). Moreover, the binding activities at the above-mentioned AR subtypes of the 1,4-dione parent compounds 26-31 and their 5-N-alkyl derivatives 33-37 were also evaluated. The substituent on the 2-phenyl ring exerted a different effect on AR subtypes, while replacement of a hydrogen atom of the 4-amino group with suitable substituents yielded selective A(1) or A(3) antagonists. Replacement of a hydrogen atom of the 4-NH2 with an acyl group, or replacement of the whole 4-NH2 with a 4-oxo moiety, shifted the binding activity toward the A(3) AR. The binding results allowed elucidation of the structural requirements for the binding of these novel tricyclic derivatives at each receptor subtype. In particular, A(1) and A(2A) binding required the presence of a proton donor group at position-4, while for A(3) affinity the presence of a proton acceptor in this same region was of paramount importance.

  DOI：

  10.1021/jm991096e
• 作为产物：
  描述：

  [(3-氟苯基)肼基]氯乙酸乙酯 在 三乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 8.0h， 生成 2-(3-Fluoro-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

• Tricyclic Heteroaromatic Systems. 1,2,4-Triazolo[4,3-a]quinoxalines and 1,2,4-Triazino[4,3-a]quinoxalines: Synthesis and Central Benzodiazepine Receptor Activity
  作者：Vittoria Colotta、Daniela Catarzi、Flavia Varano、Lucia Cecchi、Guido Filacchioni、Alessandro Galli、Chiara Costagli

  DOI：10.1002/ardp.19973301206

  日期：——

  the benzodiazepine receptor (BZR) in rat cortical membranes. The BZR affinity of 1–10 demonstrates that the presence of a proton acceptor at position‐1 is important for the potency of a BZR ligand. On the other hand, the BZR inactivity of the 1,2,5‐trione derivatives 11–12 shows that the right collocation of the essential L2 lipophilic substituent is of paramount importance for receptor‐ligand interaction

  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。
• 1,2,4-Triazolo[4,3-<i>a</i>]quinoxalin-1-one:  A Versatile Tool for the Synthesis of Potent and Selective Adenosine Receptor Antagonists
  作者：Vittoria Colotta、Daniela Catarzi、Flavia Varano、Lucia Cecchi、Guido Filacchioni、Claudia Martini、Letizia Trincavelli、Antonio Lucacchini

  DOI：10.1021/jm991096e

  日期：2000.3.1

  4-Amino-6-benzylamino-1,2-dihydro-2-phenyl-1,2,4-triazolo[4,3-a]quinoxalin-1-one (1) has been found to be an A(2A) versus A(1) selective antagonist (Colotta et al. Arch. Pharm. Pharm. Med. Chem. 1999,332, 39-41). In this paper some novel triazoloquinoxalin-1-ones 4-25 bearing different substituents on the 2-phenyl and/or 4-amino moiety of the parent 4-amino-1,2-dihydro-2-phenyl-1,2,4-triazolo[4,3-a]quinoxalin-1-one (3) have been synthesized and tested in radioligand binding assays at bovine A(1) and A(2A) and cloned human A(3) adenosine receptors (AR). Moreover, the binding activities at the above-mentioned AR subtypes of the 1,4-dione parent compounds 26-31 and their 5-N-alkyl derivatives 33-37 were also evaluated. The substituent on the 2-phenyl ring exerted a different effect on AR subtypes, while replacement of a hydrogen atom of the 4-amino group with suitable substituents yielded selective A(1) or A(3) antagonists. Replacement of a hydrogen atom of the 4-NH2 with an acyl group, or replacement of the whole 4-NH2 with a 4-oxo moiety, shifted the binding activity toward the A(3) AR. The binding results allowed elucidation of the structural requirements for the binding of these novel tricyclic derivatives at each receptor subtype. In particular, A(1) and A(2A) binding required the presence of a proton donor group at position-4, while for A(3) affinity the presence of a proton acceptor in this same region was of paramount importance.