Faculty of Chemistry-Biology, Karshi State University, 130100, Karshi, Uzbekistan.
Chemical & Materials Engineering, New Uzbekistan University, 54 Mustaqillik Ave, 100007, Tashkent, Uzbekistan.
J Mol Model. 2024 Oct 2;30(11):359. doi: 10.1007/s00894-024-06157-y.
This study addresses the development of sustainable pyridinium ionic liquids (ILs) because of their potential applications in agriculture and pharmaceuticals. Pyridinium-based ILs are known for their low melting points, high thermal stability, and moderate solvation properties. We synthesized three novel pyridinium-based ILs: 1-(2-(isopentyloxy)-2-oxoethyl)pyridin-1-ium chloride, 1-(2-(hexyloxy)-2-oxoethyl)pyridin-1-ium chloride, and 1-(2-(benzyloxy)-2-oxoethyl)pyridin-1-ium chloride. The biological activities of these compounds were evaluated through plant growth promotion, herbicidal, and insecticidal assays. Our results show that the benzyloxy derivative significantly enhances wheat and cucumber growth, whereas the isopentyloxy compound has potent herbicidal effects. Computational methods, including DFT calculations and molecular docking, were applied to understand the structure‒activity relationships (SARs) and mechanisms of action.
The computational techniques involved dispersion-corrected density functional theory (DFT) with the B3LYP functional and the 6-311G** basis set. Grimme's D3 corrections were included to account for dispersion interactions. The calculations were performed via GAMESS-US software. Quantum descriptors of reactivity, such as ionization potential, electron affinity, chemical potential, and electrophilicity index, were derived from the HOMO and LUMO energies. Molecular docking studies were conducted via the CB-Dock server via AutoDock Vina software to predict binding affinities to cancer-related proteins. Petra/Osiris/Molinspiration (POM) analysis was used to predict the drug likeness and other pharmaceutical properties of the synthesized ILs.
本研究致力于开发可持续的吡啶鎓离子液体（ILs），因为它们在农业和制药领域有潜在的应用。基于吡啶鎓的 ILs 以其低熔点、高热稳定性和中等溶解性能而闻名。我们合成了三种新型吡啶鎓基 ILs：1-(2-(异戊氧基)-2-氧代乙基)吡啶-1-鎓氯化物、1-(2-(己氧基)-2-氧代乙基)吡啶-1-鎓氯化物和 1-(2-(苄氧基)-2-氧代乙基)吡啶-1-鎓氯化物。通过植物生长促进、除草和杀虫测定评估了这些化合物的生物活性。我们的结果表明，苄氧基衍生物显著促进了小麦和黄瓜的生长，而异戊氧基化合物具有很强的除草效果。应用计算方法，包括密度泛函理论（DFT）计算和分子对接，来理解结构-活性关系（SARs）和作用机制。
计算技术涉及使用 B3LYP 函数和 6-311G**基组进行修正的分散密度泛函理论（DFT）。包含 Grimme 的 D3 校正以考虑分散相互作用。计算通过 GAMESS-US 软件进行。从 HOMO 和 LUMO 能量中得出了反应性的量子描述符，例如电离势、电子亲合势、化学势和亲电性指数。通过 CB-Dock 服务器和 AutoDock Vina 软件进行分子对接研究，以预测与癌症相关蛋白的结合亲和力。Petra/Osiris/Molinspiration（POM）分析用于预测合成 ILs 的药物相似性和其他药物性质。
