(E)-2-(2-(3-nitrobenzylidene)hydrazinyl)quinoxaline | 1551492-27-3

• 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-(3-nitrobenzylidene)hydrazinyl)quinoxaline
• 英文别名: N-[(E)-(3-nitrophenyl)methylideneamino]quinoxalin-2-amine
• CAS: 1551492-27-3
• 化学式: C₁₅H₁₁N₅O₂
• 分子量: 293.285
• InChiKey: YKTBUCSFOYCSNF-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-(3-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

• 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.