Kuş Canan, Ayhan-Kilcigil Gülgün, Ozbey Süheyla, Kaynak F Betül, Kaya Melek, Coban Tülay, Can-Eke Benay
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ankara University, 06100 Ankara, Turkey.
Bioorg Med Chem. 2008 Apr 15;16(8):4294-303. doi: 10.1016/j.bmc.2008.02.077. Epub 2008 Feb 29.
Some novel 1-methyl-4-(2-(2-substitutedphenyl-1H-benzimidazol-1-yl)acetyl)thiosemicarbazides (16a-20a), 5-[(2-(substitutedphenyl)-1H-benzimidazol-1-yl)methyl]-N-methyl-1,3,4-thiadiazol-2-amines (17b-20b), and 5-[(2-(substitutedphenyl)-1H-benzimidazol-1-yl)methyl-4-methyl-2H-1,2,4-triazole-3(4H)-thiones (16c-20c) were synthesized and tested for antioxidant properties by using various in vitro systems. Compounds 16a-20a were found to be a good scavenger of DPPH radical (IC(50), 26 microM; IC(50), 30 microM; IC(50), 43 microM; IC(50), 55 microM; IC(50), 74 microM, respectively) when compared to BHT (IC(50), 54 microM). Noteworthy results could not be found on superoxide radical. Compound 19b, which is the most active derivative inhibited slightly lipid peroxidation (28%) at 10(-3)M concentration. Compound 17c inhibited the microsomal ethoxyresorufin O-deethylase (EROD) activity with an IC(50)=4.5 x 10(-4)M which is similarly better than the specific inhibitor caffeine IC(50)=5.2 x 10(-4)M.
合成了一些新型的1-甲基-4-(2-(2-取代苯基-1H-苯并咪唑-1-基)乙酰基)硫代氨基脲(16a - 20a)、5-[(2-取代苯基)-1H-苯并咪唑-1-基甲基]-N-甲基-1,3,4-噻二唑-2-胺(17b - 20b)和5-[(2-取代苯基)-1H-苯并咪唑-1-基甲基-4-甲基-2H-1,2,4-三唑-3(4H)-硫酮(16c - 20c)，并通过各种体外系统测试了它们的抗氧化性能。与丁基羟基甲苯(BHT，IC(50)=54 microM)相比，发现化合物16a - 20a是二苯基苦味酰基自由基的良好清除剂(IC(50)分别为26 microM、30 microM、43 microM、55 microM、74 microM)。在超氧自由基方面未发现值得注意的结果。活性最高的衍生物化合物19b在10(-3)M浓度下对脂质过氧化有轻微抑制作用(28%)。化合物17c抑制微粒体乙氧基异吩恶唑酮O-脱乙基酶(EROD)活性，IC(50)=4.5×10(-4)M，同样优于特异性抑制剂咖啡因(IC(50)=5.2×10(-4)M)。
