2-oxo-1,2-dihydroquinoline-4-carboxylate 衍生物的合成、晶体结构、光谱表征、Hirshfeld 表面分析、分子对接研究和 DFT 计算以及抗氧化活性,Journal of Molecular Structure

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2-oxo-1,2-dihydroquinoline-4-carboxylate 衍生物的合成、晶体结构、光谱表征、Hirshfeld 表面分析、分子对接研究和 DFT 计算以及抗氧化活性
Journal of Molecular Structure ( IF 4.0 ) Pub Date : 2019-07-01 , DOI: 10.1016/j.molstruc.2019.03.103
Yassir Filali Baba , Yusuf Sert , Youssef Kandri Rodi , Sonia Hayani , Joel T. Mague , Damien Prim , Jerome Marrot , Fouad Ouazzani Chahdi , Nada Kheira Sebbar , El Mokhtar Essassi

摘要一系列氢喹啉衍生物 (2a-2c) 已通过环缩合反应获得。2-氧代 -1,2-二氢喹啉-4-羧酸衍生物 (3a-3c) 的合成已在相转移催化 (PTC) 条件下使用烷基化反应进行。制备的产物通过光谱 NMR 1H 和 13C、IR 和单晶 X 射线衍射技术进行表征。实现了 2D 和 3D Hirshfeld 表面（对于 3a 和 3b）研究，以了解化合物固相晶体堆积中的非键合分子间相互作用。通过优化的结构，获得并评估了最高占据分子轨道（HOMO）和最低未占据分子轨道（LUMO）能量和云。在计算结果和实验数据之间发现了良好的一致性。此外，进行分子对接研究以使用 Auto-Dock Vina 程序研究合成分子（3a 和 3b）与 1M17 抑制剂的结合模式。化合物 (3a-3c) 的抗氧化活性已使用 DPPH 自由基清除、铁还原 (FRAP) 能力和 β-胡萝卜素动力学热烫试验进行评估。DPPH 和 FRAP 方法均证实 3b 具有最好的抗氧化活性，其次是 3c。另一方面，β-胡萝卜素漂白试验表明产物 3a 具有高活性。DPPH 和 FRAP 方法均证实 3b 具有最好的抗氧化活性，其次是 3c。另一方面，β-胡萝卜素漂白试验表明产物 3a 具有高活性。DPPH 和 FRAP 方法均证实 3b 具有最好的抗氧化活性，其次是 3c。另一方面，β-胡萝卜素漂白试验表明产物 3a 具有高活性。

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Synthesis, crystal structure, spectroscopic characterization, Hirshfeld surface analysis, molecular docking studies and DFT calculations, and antioxidant activity of 2-oxo-1,2-dihydroquinoline-4-carboxylate derivatives

Abstract A series of hydroquinolines derivatives (2a-2c) have been achieved by a cyclocondensation reaction. The synthesis of 2-oxo −1,2-dihydroquinoline-4-carboxylic acid derivatives (3a-3c) has been carried out using alkylation reactions under phase transfer catalysis (PTC) conditions. The prepared products were characterized through spectroscopic NMR 1H and 13C, IR and single crystal X-ray diffraction techniques. 2D and 3D Hirshfeld surfaces (for 3a and 3b) studies were realized to understand non-bonding intermolecular interactions in solid phase crystal packing of the compound. With the optimized structures, the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) energies and clouds were obtained and evaluated. Good agreement was found between the calculated results and experimental data. Furthermore, the molecular docking study is performed to investigate binding patterns of the synthesized molecules (3a and 3b) into 1M17 inhibitor using Auto-Dock Vina program. The antioxidant activity of compounds (3a-3c) has been evaluated using DPPH free radical scavenging, ferric reducing (FRAP) power and β-carotene kinetic blanching assays. Both DPPH and FRAP methods confirmed that 3b had the best antioxidant activity followed by 3c. On the other hand, β-carotene bleaching assay showed the high activity of the product 3a.

更新日期：2019-07-01

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