Douche Dhaybia, Sert Yusuf, Brandán Silvia A, Kawther Ameed Ahmed, Bilmez Bayram, Dege Necmi, Louzi Ahmed El, Bougrin Khalid, Karrouchi Khalid, Himmi Banacer
Equipe de Chimie des Plantes et de Synthèse Organique et Bioorganique-URAC23, GEOPAC, Département de Chimie, Faculté des Sciences, Université Mohammed V in Rabat, Morocco.
Sorgun Vocational School, Science and Art Faculty-Department of Physics, Yozgat Bozok University, Yozgat, Turkey.
J Mol Struct. 2021 May 15;1232:130005. doi: 10.1016/j.molstruc.2021.130005. Epub 2021 Jan 27.
A potential new drug to treat SARS-CoV-2 infections and chloroquine analogue, 5-((1H-imidazol-1-yl)methyl)quinolin-8-ol () has been here synthesized and characterized by FT-IR, H-NMR, C-NMR, ultraviolet-visible, ESI-MS and single-crystal X-ray diffraction. was optimized in gas phase, aqueous and DMSO solutions using hybrid B3LYP/6-311++G(d,p) method. Comparisons between experimental and theoretical infrared spectra, H and C NMR chemical shifts and electronic spectrum in DMSO solution evidence good concordances. Higher solvation energy was observed in aqueous solution than in DMSO, showing in aqueous solution a higher value than antiviral brincidofovir and chloroquine. on Bond orders, atomic charges and topological studies suggest that imidazole ring play a very important role in the properties of . NBO and AIM analyses support the intra-molecular O15-H16•••N17 bonds of in the three media. Low gap value supports the higher reactivity of DD1 than chloroquine justified by the higher electrophilicity and low nucleophilicity. Complete vibrational assignments of in gas phase and aqueous solution are reported together with the scaled force constants. In addition, better intermolecular interactions were observed by Hirshfeld surface analysis. Finally, the molecular docking mechanism between ligand and COVID-19/6WCF and COVID-19/6Y84 receptors were studied to explore the binding modes of these compounds at the active sites. Molecular docking results have shown that the molecule can be considered as a potential agent against COVID-19/6Y84-6WCF receptors.
一种用于治疗SARS-CoV-2感染的潜在新药——氯喹类似物5-((1H-咪唑-1-基)甲基)喹啉-8-醇（）已在此合成，并通过傅里叶变换红外光谱（FT-IR）、氢核磁共振（H-NMR）、碳核磁共振（C-NMR）、紫外可见光谱、电喷雾电离质谱（ESI-MS）和单晶X射线衍射进行了表征。使用杂化B3LYP/6-311++G(d,p)方法在气相、水溶液和二甲基亚砜（DMSO）溶液中对进行了优化。实验红外光谱、氢和碳核磁共振化学位移以及DMSO溶液中的电子光谱之间的比较表明具有良好的一致性。观察到在水溶液中的溶剂化能高于在DMSO中，表明在水溶液中的值高于抗病毒药物布林西多福韦和氯喹。对键级、原子电荷和拓扑学的研究表明咪唑环在的性质中起着非常重要的作用。自然键轨道（NBO）和分子中的原子（AIM）分析支持在三种介质中的分子内O15-H16•••N17键。低能隙值支持DD1比氯喹具有更高的反应活性，这通过更高的亲电性和低亲核性得以证明。报告了在气相和水溶液中的完整振动归属以及标度力常数。此外，通过 Hirshfeld表面分析观察到了更好的分子间相互作用。最后，研究了配体与COVID-19/6WCF和COVID-19/6Y84受体之间的分子对接机制，以探索这些化合物在活性位点的结合模式。分子对接结果表明该分子可被视为一种针对COVID-19/6Y84 - 6WCF受体的潜在药物。
