This work describes the synthesis of eight different 6-nitro-1,4-disubstituted-quinoxaline-2,3‑dione derivatives (). The starting material, 6-nitroquinoxaline-2,3‑dione was prepared by reacting 4-nitro-phenylenediamine with oxalic acid at reflux in hydrochloric acid. Compound was alkylated with various alkyl halides under solid-liquid phase transfer catalysis (PTC) to give the dialkyl quinoxalines (. The structures of all compounds obtained were elucidated based on spectroscopic measurements: H, C NMR, MS and UV spectroscopy and confirmed by single-crystal X-ray diffraction studies in the case of and The geometrical parameters and spectral data were also compared with those of a DFT geometry optimization and molecular orbital calculation at the B3LYP/6–311++ (d, p) level of theory. The closest contacts between the molecules of the four structures were investigated by analyzing their Hirshfeld surfaces and docking investigations in the protein EGFR (pdbid: 4HJO). Moreover, the experimental results are correlated to the calculated ones and showed great compatibility. Cell proliferation was used to measure the immunomodulatory activity of compared to a control consisting only of normal cells cultured alone to determine their antiproliferative screening which concluded that the quinoxaline derivatives and showed immunomodulatory potential.

中文翻译：

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新型6-硝基喹喔啉-2,3-二酮衍生物的实验和理论研究：合成、表征、DFT计算、ADME分析、赫什菲尔德表面计算、分子对接研究和抗增殖评估


这项工作描述了八种不同的 6-硝基-1,4-二取代-喹喔啉-2,3-二酮衍生物的合成 ()。起始原料 6-硝基喹喔啉-2,3-二酮是通过 4-硝基苯二胺与草酸在盐酸中回流反应制备的。在固-液相转移催化 (PTC) 下，化合物与各种烷基卤化物进行烷基化，得到二烷基喹喔啉 (。基于光谱测量：H、C NMR、MS 和 UV 光谱阐明了所得所有化合物的结构，并通过单一方法证实- 和 情况下的晶体 X 射线衍射研究 几何参数和光谱数据也与 B3LYP/6–311++ (d, p) 理论水平上的 DFT 几何优化和分子轨道计算的数据进行了比较。通过分析其赫什菲尔德表面和蛋白质EGFR（pdbid：4HJO）中的对接研究，研究了四种结构的分子之间的最紧密接触，此外，实验结果与计算结果相关，并且显示出良好的细胞增殖兼容性。测量与仅由单独培养的正常细胞组成的对照相比的免疫调节活性，以确定其抗增殖筛选，其结论是喹喔啉衍生物并显示出免疫调节潜力。