Nobre Patrick C, Borges Elton L, Silva Cristian M, Casaril Angela M, Martinez Débora M, Lenardão Eder J, Alves Diego, Savegnago Lucielli, Perin Gelson
Laboratório de Síntese Orgânica Limpa-LASOL, CCQFA, Universidade Federal de Pelotas-UFPel, CEP 96010-900 Pelotas, RS, Brazil.
Grupo de Pesquisa em Neurobiotecnologia-GPN, CDTec, Unidade Biotecnologia, Universidade Federal de Pelotas, UFPel, CEP 96010-900 Pelotas, RS, Brazil.
Bioorg Med Chem. 2014 Nov 1;22(21):6242-9. doi: 10.1016/j.bmc.2014.08.018. Epub 2014 Aug 27.
We describe here a simple method for the synthesis of glycerol derivatives containing an organochalcogen unit (Se, Te and S) using NaBH4 and PEG-400 as a solvent. The new methodology was used to synthesize a range of new organochalcogen compounds in good yields. Furthermore, four of synthesized compounds were evaluated for their antioxidant activity using different assays, such as 2-azinobis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS), 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical, nitric oxide (NO) and hydroxyl radical (OH) scavenging, ferric ion reducing antioxidant power (FRAP), ferrous ion chelating, superoxide dismutase-like activity and inhibition of linoleic acid lipid peroxidation. The new organotellurium 2,2-dimethyl-4-(phenyltellanylmethyl)-1,3-dioxolane 3 j showed antioxidant activity and was more effective in inhibition of induced lipid peroxidation compared to solketal 4. Selenium and sulfur analogs 3a and 3m and solketal 4 did not present antioxidant effect. These findings suggest that 2,2-dimethyl-4-(phenyltellanylmethyl)-1,3-dioxolane 3 j is a promising antioxidant and that its activity is influenced by the presence of the tellurium atom on the structure.
我们在此描述一种使用硼氢化钠和聚乙二醇 - 400作为溶剂合成含有有机硫属元素单元（硒、碲和硫）的甘油衍生物的简单方法。该新方法用于以良好的产率合成一系列新型有机硫属元素化合物。此外，使用不同的测定方法评估了四种合成化合物的抗氧化活性，例如2 - 偶氮二（3 - 乙基苯并噻唑啉 - 6 - 磺酸）（ABTS）、2,2 - 二苯基 - 1 - 苦基肼基（DPPH）自由基、一氧化氮（NO）和羟基自由基（OH）清除、铁离子还原抗氧化能力（FRAP）、亚铁离子螯合、超氧化物歧化酶样活性以及对亚油酸脂质过氧化的抑制作用。新型有机碲化合物2,2 - 二甲基 - 4 - （苯基碲基甲基） - 1,3 - 二氧戊环3j显示出抗氧化活性，并且与缩酮4相比，在抑制诱导的脂质过氧化方面更有效。硒和硫类似物3a和3m以及缩酮4没有呈现抗氧化作用。这些发现表明2,2 - 二甲基 - 4 - （苯基碲基甲基） - 1,3 - 二氧戊环3j是一种有前景的抗氧化剂，并且其活性受结构中碲原子的存在影响。
