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Synthesis, characterization, and antioxidant activity of some ebselen analogues

机译：一些EBSelen类似物的合成，表征和抗氧化活性

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摘要

Simple synthetic routes for several analogues of the anti-inflammatory organoselenium drug, ebselen, are described. The compounds are characterized by H-1, C-13, and Se-77 NMR spectroscopy and mass spectral techniques and, in some cases, by single-crystal Xray diffraction studies. The glutathione peroxidase (GPx)-like antioxidant activity has been studied by using H2O2, tBuOOH, and Cum-OOH as substrates, and thiophenol (PhSH, 4-MeC6H4SH) and glutathione (GSH) as cosubstrates. Density functional theory (DFT) calculations have been performed on these systems to understand the effects of various substituents on the Se-77 NMR chemical shifts; these results have been compared with the experimental data. The experimental and theoretical results suggest that the presence of a phenyl substituent on the nitrogen atom is important for the antioxidant activity of ebselen. While ebselen and its analogues are poor catalysts in aromatic thiol assays, these compounds exhibit high GPx activity when GSH is used as the cosubstrate. The poor catalytic activity of ebselen analogues in the presence of aromatic thiols such as PhSH and 4-Me-C6H4SH can be ascribed to the undesired thiol exchange reaction that takes place at the selenium center due to Se center dot center dot center dot O non-bonding interactions. To understand the effects of different peroxides on the catalytic activities, we have determined the initial rates at various concentrations of GSH and peroxides. These data suggest that the nature of peroxide has little effect on the catalytic efficiencies, although the initial reaction rates observed with hydrogen peroxide were found to be higher than that with tBuOOH and Cum-OOH. In contrast to the effect of peroxides, the nature of thiols appears to have a dramatic effect on the catalytic activity of ebselen and its related derivatives.
机译：描述了抗炎有机烯类药物，EBSelen的几种类似物的简单合成途径。化合物的特征在于H-1，C-13和SE-77 NMR光谱和质谱技术，并且在某些情况下，通过单晶X射线衍射研究。已经通过使用H 2 O 2，TBUOOH和CUM-OOH作为基质和噻吩醇（PHSH，4-MEC6H4SH）和谷胱甘肽（GSH）作为补充剂来研究谷胱甘肽过氧化物酶（GPX） - 样抗氧化活性。已经对这些系统进行了密度泛函理论（DFT）计算，以了解各种取代基对SE-77 NMR化学位移的影响;这些结果已经与实验数据进行了比较。实验和理论结果表明，氮原子上的苯基取代基对EBSelen的抗氧化活性很重要。虽然EBSELEN及其类似物是芳族硫醇测定中的催化剂差，但是当GSH用作烯库时，这些化合物表现出高GPX活性。在芳族硫醇如Phsh和4-Me-C6H4s中存在eBSelen类似物的催化活性差可归因于由于SE中心点中心点中心点O非 - 硒中心在硒中心发生的不需要的硫醇交换反应。粘接相互作用。为了了解不同过氧化物对催化活性的影响，我们已经确定了各种浓度的GSH和过氧化物的初始速率。这些数据表明过氧化物的性质对催化效率影响不大，尽管发现用过氧化氢观察到的初始反应速率高于TBUOOH和CUM-OOH的初始反应速率。与过氧化物的影响相反，硫醇的性质似乎对EBSelen及其相关衍生物的催化活性具有显着影响。

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