Quinoline-imidazo[1,2-a]pyridine conjugates as potential antioxidant agents: Synthesis, experimental and theoretical approaches

IF 4.9 2区化学 Q2 CHEMISTRY, PHYSICAL

Journal of Molecular Structure Pub Date : 2026-05-15 Epub Date: 2026-02-09 DOI:10.1016/j.molstruc.2026.145622

Houria Bouria , Hayette Alliouche , Arif Mermer , Yakup Sirin , Burak Tüzün , Rafik Bensegueni , Mohamed Imed Chouiter , Hasan Küçükbay , Ali Belfaitah

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引用次数: 0

Abstract

N-heterocyclic compounds such as quinolines and imidazopyridines are very important structures in medicinal chemistry, especially for drug development. In this work, a series of novel quinoline-imidazo[1,2-a]pyridines hybrids (IMP1-10) were synthesized from 3-(quinolin-3-yl) oxirane-2,2-carbonitriles (1-10) via a nucleophilic ring-opening reaction and were characterized by conventional analytical techniques. The antioxidant capacity of the synthesized compounds was investigated using the DPPH, FRAP and ABTS methods, and it was found that IMP-7 exhibited the best DPPH and FRAP activity with an IC₅₀ values of 0,33 ± 0,05 µM and 2387,45 ± 23,25 μmol TE/g, respectively. In the course of the analysis of the ABTS assay results, IMP-10 was found to demonstrate the highest activity, with an IC₅₀ value of 0.67 ± 0.04 µM. The antioxidant mechanism properties of the most potent compounds IMP-7, IMP-8 and IMP-10 were calculated with the Gaussian package program using HF/6-31++G(d,p) basis set.

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喹啉-咪唑[1,2-a]吡啶缀合物作为潜在的抗氧化剂：合成、实验和理论方法

n -杂环化合物，如喹啉类和咪唑吡啶类，是药物化学中非常重要的结构，特别是在药物开发中。本文以3-（喹啉-3-基）氧烷-2,2-碳腈（1-10）为原料，通过亲核开环反应合成了一系列新型喹啉-咪唑[1,2-a]吡啶杂化物（IMP1-10），并用常规分析技术对其进行了表征。采用DPPH、FRAP和ABTS法对合成化合物的抗氧化能力进行了研究，结果表明，IMP-7的DPPH和FRAP活性最高，IC50值分别为0.33±0.05µM和2387、45±23,25 μmol TE/g。在ABTS检测结果的分析过程中，发现IMP-10的活性最高，IC50值为0.67±0.04µM。采用HF/6-31++G（d,p）基集，利用高斯包程序计算了最有效化合物IMP-7、IMP-8和IMP-10的抗氧化机理。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Journal of Molecular Structure 化学-物理化学

CiteScore

7.10

自引率

15.80%

发文量

2384

审稿时长

45 days

期刊介绍： The Journal of Molecular Structure is dedicated to the publication of full-length articles and review papers, providing important new structural information on all types of chemical species including: • Stable and unstable molecules in all types of environments (vapour, molecular beam, liquid, solution, liquid crystal, solid state, matrix-isolated, surface-absorbed etc.) • Chemical intermediates • Molecules in excited states • Biological molecules • Polymers. The methods used may include any combination of spectroscopic and non-spectroscopic techniques, for example: • Infrared spectroscopy (mid, far, near) • Raman spectroscopy and non-linear Raman methods (CARS, etc.) • Electronic absorption spectroscopy • Optical rotatory dispersion and circular dichroism • Fluorescence and phosphorescence techniques • Electron spectroscopies (PES, XPS), EXAFS, etc. • Microwave spectroscopy • Electron diffraction • NMR and ESR spectroscopies • Mössbauer spectroscopy • X-ray crystallography • Charge Density Analyses • Computational Studies (supplementing experimental methods) We encourage publications combining theoretical and experimental approaches. The structural insights gained by the studies should be correlated with the properties, activity and/ or reactivity of the molecule under investigation and the relevance of this molecule and its implications should be discussed.