(E)-2-(2-(2-chlorobenzylidene)hydrazinyl)quinoxaline

• 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-chlorobenzylidene)hydrazinyl)quinoxaline
• 英文别名: (E)-2-[2-(2-chlorobenzylidene)hydrazinyl]quinoxaline；N-[(E)-(2-chlorophenyl)methylideneamino]quinoxalin-2-amine
• 化学式: C₁₅H₁₁ClN₄
• 分子量: 282.732
• InChiKey: BCLAHJQULOTPBC-GIJQJNRQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 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：
  50.2
• 氢给体数：
  1
• 氢受体数：
  4

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-(2-chlorobenzylidene)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

• Comparison of the structure of (<i>E</i>)-2-(2-benzylidenehydrazinylidene)quinoxaline with those of its chloro- and bromobenzylidene analogues
  作者：Ligia Rebelo Gomes、John Nicolson Low、Ana S. M. C. Rodrigues、James L. Wardell、Marcus V. N. de Souza、Thais C. M. Noguiera、Alessandra C. Pinheiro

  DOI：10.1107/s0108270113015370

  日期：2013.8.15

  (E)-2-(2-Benzylidenehydrazinylidene)quinoxaline, C₁₅H₁₂N₄, crystallized with two molecules in the asymmetric unit. The structures of six halogen derivatives of this compound were also investigated: (E)-2-[2-(2-chlorobenzylidene)hydrazinylidene]quinoxaline, C₁₅H₁₁ClN₄; (E)-2-[2-(3-chlorobenzylidene)hydrazinylidene]quinoxaline, C₁₅H₁₁ClN₄; (E)-2-[2-(4-chlorobenzylidene)hydrazinylidene]quinoxaline, C₁₅H₁₁ClN₄; (E)-2-[2-(2-bromobenzylidene)hydrazinylidene]quinoxaline, C₁₅H₁₁BrN₄; (E)-2-[2-(3-bromobenzylidene)hydrazinylidene]quinoxaline, C₁₅H₁₁BrN₄; (E)-2-[2-(4-bromobenzylidene)hydrazinylidene]quinoxaline, C₁₅H₁₁BrN₄. The 3-Cl and 3-Br compounds are isomorphous, as are the 4-Cl and 4-Br compounds. In all of these compounds, it was found that the supramolecular structures are governed by similar predominant patterns,viz.strong intermolecular N—H...N(pyrazine) hydrogen bonds supplemented by weak C—H...N(pyrazine) hydrogen-bond interactions in the 2- and 3-halo compounds and by C—H...Cl/Br interactions in the 4-halo compounds. In all compounds, there are π–π stacking interactions.

  (E)-2-(2-亚苄基肼亚基)喹喔啉，C15H12N4，在不对称单元中结晶出两个分子。此外，还研究了该化合物的六种卤素衍生物的结构：(E)-2-[2-(2-氯亚苄基)亚肼]喹喔啉，C15H11ClN4；(E)-2-[2-(3-氯亚苄基)亚肼]喹喔啉， ；(E)-2-[2-(4-氯亚苄基)亚肼]喹喔啉， ；(E)-2-[2-(2-溴亚苄基)肼亚基]喹喔啉，C15H11BrN4； (E)-2-[2-(3-溴亚苄基)肼亚基]喹喔啉， ； (E)-2-[2-(4-溴亚苄基)肼亚基]喹喔啉， 。3-Cl 和 3-Br 化合物是同构物，4-Cl 和 4-Br 化合物也是同构物。在所有这些化合物中，发现超分子结构受类似的主要模式支配，即在 2-卤素和 3-卤素化合物中，分子间的 N-H...N（吡嗪）氢键较强，辅以弱的 C-H...N（吡嗪）氢键相互作用；在 4-卤素化合物中，分子间的 C-H...Cl/Br 相互作用较弱。在所有化合物中，都存在 π-π 堆积相互作用。
• 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.