Bailly Fabrice, Maurin Cédric, Teissier Elisabeth, Vezin Hervé, Cotelle Philippe
Laboratoire de Chimie Organique et Macromoléculaire, UMR CNRS 8009, Bâtiment C3, Université de Lille 1, 59655 Villeneuve d'Ascq Cedex, France.
Bioorg Med Chem. 2004 Nov 1;12(21):5611-8. doi: 10.1016/j.bmc.2004.07.066.
A series of hydroxylated 3-hydroxycoumarins was synthesised by the reaction of 3-aryl-2-hydroxypropenoic derivatives with boron tribromide. They were evaluated for their ability to scavenge the 2,2-diphenyl-1-picrylhydrazyl radical, the superoxide anion radical, the hydroxyl radical and the peroxynitrite anion and to inhibit copper-induced human LDL peroxidation. The physicochemical results were in accordance to establish the compounds hydroxylated on C-6 and C-7 positions as the most active of the series with antioxidant potencies comparable to those of quercetin and vitamin C. These compounds form o- and p-quinonoid derivatives upon radical scavenging and may serve as new lead compounds for pharmacological investigations.
通过3-芳基-2-羟基丙烯酸衍生物与三溴化硼反应合成了一系列羟基化的3-羟基香豆素。对它们清除2,2-二苯基-1-苦基肼自由基、超氧阴离子自由基、羟基自由基和过氧亚硝酸盐阴离子的能力以及抑制铜诱导的人低密度脂蛋白过氧化的能力进行了评估。物理化学结果表明，该系列中C-6和C-7位羟基化的化合物活性最高，其抗氧化能力与槲皮素和维生素C相当。这些化合物在清除自由基时形成邻醌和对醌衍生物，可作为药理学研究的新先导化合物。
