Synthesis and antioxidant properties of novel N-methyl-1,3,4-thiadiazol-2-amine and 4-methyl-2H-1,2,4-triazole-3(4H)-thione derivatives of benzimidazole class
Synthesis and antioxidant properties of novel N-methyl-1,3,4-thiadiazol-2-amine and 4-methyl-2H-1,2,4-triazole-3(4H)-thione derivatives of benzimidazole class
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DOI：
10.1016/j.bmc.2008.02.077
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发表时间：
2008-04-15
影响因子：
3.5
通讯作者：
Can-Eke, Benay
中科院分区：
文献类型：
--
作者：
Kus, Canan;Ayhan-Kilcigil, Gulgun;Can-Eke, Benay
合成了一些新的1-甲基-4-（2-（2-取代苯基）1h -苯并咪唑-1-酰基）乙酰基)硫代氨基脲（16a-20a）、5-[（2-（取代苯基）1h -苯并咪唑-1-酰基）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-酰基）甲基-4-甲基- 2h -1,2,4-三唑-3(4H)-硫酮（16c-20c），并通过各种体外体系测试了它们的抗氧化性能。与BHT （IC50, 54 μ M）相比，化合物16a-20a具有较好的DPPH自由基清除率（IC50, 26 μ M; IC50, 30 μ M; IC50, 43 μ M; IC50, 55 μ M; IC50, 74 μ M）。在超氧自由基上没有发现值得注意的结果。化合物19b是活性最强的衍生物，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抑制微粒体乙氧基间苯二酚o -去乙基酶（EROD）活性的IC50 = 4.5 × 10(-4) M，与特异性抑制剂咖啡因的IC50 = 5.2 × 10(-4) M相似(C) 2008 Elsevier Ltd.。版权所有。
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 (IC50, 26 mu M; IC50, 30 mu M; IC50, 43 mu M; IC50, 55 mu M; IC50, 74 mu M, respectively) when compared to BHT (IC50, 54 mu M). 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 IC50 = 4.5 x 10(-4) M which is similarly better than the specific inhibitor caffeine IC50 = 5.2 x 10(-4) M. (C) 2008 Elsevier Ltd. All rights reserved.