El-Saghier Ahmed M, El-Naggar Mohamed, Hussein Abdel Haleem M, El-Adasy Abu-Bakr A, Olish M, Abdelmonsef Aboubakr H
Chemistry Department, Faculty of Science, Sohag University, Sohag, Egypt.
Chemistry Department, Faculty of Sciences, University of Sharjah, Sharjah, United Arab Emirates.
Front Chem. 2021 Jun 10;9:679967. doi: 10.3389/fchem.2021.679967. eCollection 2021.
A new series of quinoline derivatives were efficiently synthesized one-pot multicomponent reaction (MCR) of resorcinol, aromatic aldehydes, β-ketoesters, and aliphatic/aromatic amines under solvent-free conditions. All products were obtained in excellent yields, pure at low-cost processing, and short time. The structures of all compounds were characterized by means of spectral and elemental analyses. In addition, all the synthesized compounds were screened for their antioxidant and antibacterial activity. Moreover, molecular docking studies of the new quinoline derivatives with the target enzymes, human NAD (P)H dehydrogenase (quinone 1) and DNA gyrase, were achieved to endorse their binding affinities and to understand ligand-enzyme possible intermolecular interactions. Compound displayed promising antioxidant and antibacterial activity, as well as it was found to have the highest negative binding energy of -9.1 and -9.3 kcal/mol for human NAD (P)H dehydrogenase (quinone 1) and DNA gyrase, respectively. Further, it complied with the Lipinski's rule of five, Veber, and Ghose. Therefore, the quinoline analogue could be promising chemical scaffold for the development of future drug candidates as antioxidant and antibacterial agents.
在无溶剂条件下，通过间苯二酚、芳香醛、β-酮酯和脂肪族/芳香族胺的一锅多组分反应（MCR）高效合成了一系列新的喹啉衍生物。所有产物均以优异的产率获得，成本低廉且加工简便，反应时间短。所有化合物的结构均通过光谱和元素分析进行了表征。此外，对所有合成化合物的抗氧化和抗菌活性进行了筛选。此外，还对新喹啉衍生物与靶标酶——人NAD（P）H脱氢酶（醌1）和DNA促旋酶进行了分子对接研究，以确认它们的结合亲和力，并了解配体与酶之间可能的分子间相互作用。化合物表现出有前景的抗氧化和抗菌活性，并且发现其与人NAD（P）H脱氢酶（醌1）和DNA促旋酶的负结合能分别为-9.1和-9.3千卡/摩尔，是最高的。此外，它符合Lipinski的五规则、Veber规则和Ghose规则。因此，喹啉类似物可能是开发未来作为抗氧化剂和抗菌剂的候选药物的有前景的化学骨架。
