(E)-2-(2-(2-nitrobenzylidene)hydrazinyl)quinoxaline | 1551492-24-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (E)-2-(2-(2-nitrobenzylidene)hydrazinyl)quinoxaline
• 英文别名: N-[(E)-(2-nitrophenyl)methylideneamino]quinoxalin-2-amine
• CAS: 1551492-24-0
• 化学式: C₁₅H₁₁N₅O₂
• 分子量: 293.285
• InChiKey: UFQSPZDQMHVBLA-RQZCQDPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  96
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-2-(2-(2-nitrobenzylidene)hydrazinyl)quinoxaline 在 selenium(IV) oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以93%的产率得到1-(2-nitrophenyl)-[1,2,4]triazolo[4,3-a]quinoxaline
  参考文献：
  名称：

  二氧化硒介导的融合 1,2,4-三唑作为细胞毒性剂的合成

  摘要：

  摘要 通过杂环腙与二氧化硒分子内氧化环化反应制备了一系列稠合1,2,4-三唑类化合物。该实用方案的普遍适用性通过中等至良好产率的 1,2,4-三唑并 [4,3-a] 吡啶、1,2,4-三唑并 [4,3-a] 嘧啶的合成得到证实，1 ,2,4-三唑并[4,3-a] 嘧啶和 1,2,4-三唑并-[4,3-a] 喹喔啉系。在体外测试了所有化合物对 HCT-116、A549 和 Colo-205 细胞系的细胞毒活性。两种化合物，3-(4-甲氧基苯基)-7-甲基-[1,2,4]三唑并[4,3-a]吡啶和1-(4-甲氧基苯基)-[1,2,4]三唑并[4] ,3-a]喹喔啉对三种细胞系显示出有效的抗增殖活性。图形概要

  DOI：

  10.1080/00397911.2015.1111384
• 作为产物：
  描述：

  2-氯喹恶啉 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 72.0h， 生成 (E)-2-(2-(2-nitrobenzylidene)hydrazinyl)quinoxaline
  参考文献：
  名称：

  Design, synthesis and biological evaluation of (E)-2-(2-arylhydrazinyl)quinoxalines, a promising and potent new class of anticancer agents

  摘要：

  A series of forty-seven quinoxaline derivatives, 2-(XYZC(6)H(2)CH@N-NH)-quinoxalines, 1, have been synthesized and evaluated for their activity against four cancer cell lines: potent cytotoxicities were found (IC50 ranging from 0.316 to 15.749 mu M). The structure-activity relationship (SAR) analysis indicated that the number, the positions and the type of substituents attached to the aromatic ring are critical for biological activity. The activities do not depend on the electronic effects of the substituents nor on the lypophilicities of the molecules. A common feature of active compounds is an ortho-hydroxy group in the phenyl ring. A potential role of these ortho-hydroxy derivatives is as N, N, O-tridentate ligands complexing with a vital metal, such as iron, and thereby preventing proliferation of cells. The most active compound was (1: X, Y = 2,3-(OH)(2), Z = H), which displayed a potent cytotoxicity comparable to that of the reference drug doxorubicin. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.074

文献信息

• In silico binding analysis and SAR elucidations of newly designed benzopyrazine analogs as potent inhibitors of thymidine phosphorylase
  作者：Muhammad Taha、Nor Hadiani Ismail、Syahrul Imran、Fazal Rahim、Abdul Wadood、Laode Muhammad Ramadhan Al Muqarrabun、Khalid Mohammed Khan、Mehreen Ghufran、Muhammad Ali

  DOI：10.1016/j.bioorg.2016.07.010

  日期：2016.10

  Thymidine phosphorylase (TP) is up regulated in wide variety of solid tumors and therefore presents a remarkable target for drug discovery in cancer. A novel class of extremely potent TPase inhibitors based on benzopyrazine (1-28) has been developed and evaluated against thymidine phosphorylase enzyme. Out of these twenty-eight analogs eleven (11) compounds 1, 4, 14, 15, 16, 17, 18, 19, 20, 24 and 28 showed potent thymidine phosphorylase inhibitory potentials with IC50 values ranged between 3.20 +/- 0.30 and 37.60 +/- 1.15 mu M when compared with the standard 7-Deazaxanthine (IC50 = 38.68 +/- 4.42 mu M). Structure-activity relationship was established and molecular docking studies were performed to determine the binding interactions of these newly synthesized compounds. Current studies have revealed that these compounds established stronger hydrogen bonding networks with active site residues as compare to the standard compound 7DX. (C) 2016 Elsevier Inc. All rights reserved.
• Design, synthesis and biological evaluation of (E)-2-(2-arylhydrazinyl)quinoxalines, a promising and potent new class of anticancer agents
  作者：Felipe A.R. Rodrigues、Igor da S. Bomfim、Bruno C. Cavalcanti、Claudia do Ó. Pessoa、James L. Wardell、Solange M.S.V. Wardell、Alessandra C. Pinheiro、Carlos Roland Kaiser、Thais C.M. Nogueira、John N. Low、Ligia R. Gomes、Marcus V.N. de Souza

  DOI：10.1016/j.bmcl.2013.12.074

  日期：2014.2

  A series of forty-seven quinoxaline derivatives, 2-(XYZC(6)H(2)CH@N-NH)-quinoxalines, 1, have been synthesized and evaluated for their activity against four cancer cell lines: potent cytotoxicities were found (IC50 ranging from 0.316 to 15.749 mu M). The structure-activity relationship (SAR) analysis indicated that the number, the positions and the type of substituents attached to the aromatic ring are critical for biological activity. The activities do not depend on the electronic effects of the substituents nor on the lypophilicities of the molecules. A common feature of active compounds is an ortho-hydroxy group in the phenyl ring. A potential role of these ortho-hydroxy derivatives is as N, N, O-tridentate ligands complexing with a vital metal, such as iron, and thereby preventing proliferation of cells. The most active compound was (1: X, Y = 2,3-(OH)(2), Z = H), which displayed a potent cytotoxicity comparable to that of the reference drug doxorubicin. (C) 2013 Elsevier Ltd. All rights reserved.
• Selenium Dioxide–Mediated Synthesis of Fused 1,2,4-Triazoles as Cytotoxic Agents
  作者：Heng Zheng、Kang Wang、Wei Zhang、Ruihuan Liu

  DOI：10.1080/00397911.2015.1111384

  日期：2015.12.17

  prepared by oxidative intramolecular cyclization of heterocyclic hydrazones with selenium dioxide. General applicability of this practical protocol was confirmed by the synthesis of moderate to good yields of 1,2,4-triazolo[4,3-a]pyridines, 1,2,4-triazolo[4,3-a]pyrimidines, 1,2,4-triazolo[4,3-a]pyramidines, and 1,2,4-triazolo-[4,3-a]quinoxa lines. All compounds were tested in vitro for their cytotoxic

  摘要 通过杂环腙与二氧化硒分子内氧化环化反应制备了一系列稠合1,2,4-三唑类化合物。该实用方案的普遍适用性通过中等至良好产率的 1,2,4-三唑并 [4,3-a] 吡啶、1,2,4-三唑并 [4,3-a] 嘧啶的合成得到证实，1 ,2,4-三唑并[4,3-a] 嘧啶和 1,2,4-三唑并-[4,3-a] 喹喔啉系。在体外测试了所有化合物对 HCT-116、A549 和 Colo-205 细胞系的细胞毒活性。两种化合物，3-(4-甲氧基苯基)-7-甲基-[1,2,4]三唑并[4,3-a]吡啶和1-(4-甲氧基苯基)-[1,2,4]三唑并[4] ,3-a]喹喔啉对三种细胞系显示出有效的抗增殖活性。图形概要