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Tetrahydroquinolines as inhibitors of radical chain oxidation of organic compounds: kinetics and mechanism of action
Reaction Kinetics, Mechanisms and Catalysis ( IF 1.7 ) Pub Date : 2024-07-06 , DOI: 10.1007/s11144-024-02649-3
A. Ya. Gerchikov , I. V. Safarova , G. M. Shaymordanova , E. F. Safarov , R. G. Savchenko

The effectiveness and mechanism of the antioxidant action of a number of biologically active polysubstituted tetrahydroquinolines in a model reaction of liquid-phase oxidation of 1,4-dioxane have been studied. The research into the properties of these substances in the field of pharmacology is becoming increasingly important due to their ability to act as inhibitors of radical chain oxidation of organic compounds. The fact is that the manifestation of the antioxidant properties of biologically active compounds leads to an increase in the therapeutic effect of potential drugs. In this case, the drug, simultaneously with the function of treating the target disease, additionally slows down the rate of the undesirable process of lipid peroxidation of cell membranes. The oxidation reaction has been observed at 348 K using a manometric technique, measuring the change in the concentration of absorbed oxygen in the gas phase under different initial conditions of the studied antioxidants over time. In the presence of tetrahydroquinoline (THQ) additives, the kinetic curves of oxygen absorption exhibit an induction period (τ) when the rate of oxygen absorption is immeasurably low. The dependence of τ and the rate of inhibited oxidation on the concentration of THQ has been studied and the reaction mechanism formulated, including the stage of regeneration of the inhibitor at the stage of chain termination. Using the method of mathematical modeling, the adequacy of the mechanism to the obtained experimental data has been substantiated, the rate constants of the key stages and parameters of the efficiency of inhibitor f regeneration have been found. When comparing the results of this article with previously published data, it has been found that the mechanism and antioxidant efficiency of tetrahydroquinolines depend on their structure and the nature of the active site of inhibition.



中文翻译:


四氢喹啉作为有机化合物自由基链氧化抑制剂:动力学和作用机制



研究了多种生物活性多取代四氢喹啉在 1,4-二恶烷液相氧化模型反应中的抗氧化作用的有效性和机制。由于这些物质能够充当有机化合物自由基链氧化的抑制剂,因此在药理学领域对这些物质的性质的研究变得越来越重要。事实是,生物活性化合物的抗氧化特性的表现导致潜在药物的治疗效果增加。在这种情况下,药物在治疗目标疾病的同时,还减慢了细胞膜脂质过氧化这一不良过程的速率。使用测压技术在 348 K 下观察到氧化反应,测量所研究的抗氧化剂在不同初始条件下气相中吸收的氧浓度随时间的变化。在四氢喹啉(THQ)添加剂存在下,吸氧动力学曲线呈现出诱导期(τ),此时吸氧速率极低。研究了τ和抑制氧化速率对THQ浓度的依赖性,并制定了反应机理,包括链终止阶段抑制剂的再生阶段。利用数学建模的方法,对所获得的实验数据证实了该机理的充分性,找出了关键阶段的速率常数和抑制剂再生效率的参数。 当将本文的结果与之前发表的数据进行比较时,发现四氢喹啉的机制和抗氧化效率取决于其结构和抑制活性位点的性质。

更新日期:2024-07-07
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