新烷基（环己基）2-oxo-1-(prop-2-yn-1-yl)-1,2-dihydroquinoline-4-carboxylates：合成、晶体结构、光谱表征、Hirshfeld 表面分析、分子对接研究和 DFT计算,Journal of Molecular Structure

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新烷基（环己基）2-oxo-1-(prop-2-yn-1-yl)-1,2-dihydroquinoline-4-carboxylates：合成、晶体结构、光谱表征、Hirshfeld 表面分析、分子对接研究和 DFT计算
Journal of Molecular Structure ( IF 4.0 ) Pub Date : 2021-03-01 , DOI: 10.1016/j.molstruc.2020.129520
Sonia Hayani , Yusuf Sert , Yassir Filali Baba , Fouad Benhiba , Fouad Ouazzani Chahdi , Fatim-Zahra Laraqui , Joel T. Mague , Brahim El Ibrahimi , Nada Kheira Sebbar , Youssef Kandri Rodi , El Mokhtar Essassi

摘要以 2-oxo-quinoline 羧酸 1a 为原料，通过酯化和烷基化反应，高效合成了新型 2-oxo-1,2-dihydroquinoline-4-carboxylates (3a-3d)。通过使用 1H NMR 和 13C NMR 光谱测量研究和表征所有获得的化合物的结构。四种化合物（3a、3b、3c 和 3d）的分子和晶体结构也已通过单晶 X 射线晶体学进行了检查。此外，还使用密度泛函理论 (DFT) 在 B3LYP/6-31G(d,p) 理论水平上获得了实验数据和预测光谱数据。此外，通过 Hirshfeld 表面分析、分子对接研究和 DFT 计算确定了四种结构的活性原子之间的最密切接触。实验结果与计算结果具有相关性，显示出很好的兼容性。最后，进行分子对接研究以研究标题化合物与蛋白质数据库（PDB：1M17-EGFR 激酶）抑制剂靶标的结合模式，并使用 Auto-Dock Vina 程序对可能的相互作用进行了深入了解。

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New alkyl (cyclohexyl) 2-oxo-1-(prop-2-yn-1-yl)-1,2-dihydroquinoline-4-carboxylates: synthesis, crystal structure, spectroscopic characterization, Hirshfeld surface analysis, molecular docking studies and DFT calculations

Abstract An efficient synthesis of novel alkyl 2-oxo-1,2-dihydroquinoline-4-carboxylates (3a-3d) was developed, starting from 2-oxo-quinoline carboxylic acid 1a which successively undergoes esterification and alkylation reactions. The structures of all the obtained compounds were investigated and characterized by using 1H NMR and 13C NMR spectroscopic measurements. The molecular and crystal structures of four compounds (3a, 3b, 3c and 3d) have also been examined by single crystal X-ray crystallography. Furthermore, the experimental data and the predicted spectral data were also obtained using density functional theory (DFT) at the B3LYP/6-31G(d,p) level of theory. Also, the closest contacts between the active atoms of the four structures were identified through Hirshfeld surface analyses, molecular docking studies, and DFT calculations. The experimental results are correlated to the calculated ones and showed great compatibility. Finally, molecular docking studies are performed to investigate the binding patterns of the titled compounds with the Protein Data Bank (PDB:1M17-EGFR kinase) inhibitor targets and showed good insights on the possible interactions using the Auto-Dock Vina program.

更新日期：2021-03-01

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