摘要/Abstract

以对氨基苯甲酸为原料，经多步反应合成了16个未见文献报道的1，2，4-三唑三氮烯衍生物.利用¹H NMR，¹³C NMR和HRMS对标题化合的结构进行了表征.衍生物的细胞毒活性测试结果表明，2-[4-（3，3-二甲基三氮烯-1-基）苯基]-3-氨基-4-S-（4-氯基苄基）-1，2，4-三唑（6g）、2-[4-（3，3-二甲基三氮烯-1-基）苯基]-3-氨基-4-S-（2，4-二氯基苄基）-1，2，4-三唑（6h）、2-[4-（3，3-甲基苯甲基三氮烯-1-基）苯基]-3-氨基-4-S-苄基-1，2，4-三唑（6i）、2-[4-（3，3-甲基苯甲基三氮烯-1-基）苯基]-3-氨基-4-S-（4-甲基苄基）-1，2，4-三唑（6j）、2-[4-（3，3-甲基苯甲基三氮烯-1-基）苯基]-3-氨基-4-S-（4-甲氧基苄基）-1，2，4-三唑（6l）、2-[4-（3，3-甲基苯甲基三氮烯-1-基）苯基]-3-氨基-4-S-（2，4-二氯基苄基）-1，2，4-三唑（6p）对膀胱癌细胞具有较好的抑制作用，其IC₅₀值分别为23.883，5.512，8.731，8.077，5.590和12.195 μmol/L，化合物6h，6i，6j，6l对前列腺癌细胞具有较好的抑制作用，其IC₅₀值分别为13.690，21.908，10.772和4.827 μmol/L.
关键词: 三氮烯, 1,2,4-三唑, 合成, 抗肿瘤
Sixteen novel 1,2,4-triazole triazene derivatives were synthesized in multiple steps from the p-aminobenzoic acid. Their structures were confirmed by ¹H NMR, ¹³C NMR and HRMS. All the target compounds were evaluated for their anticancer activity. Among them, 2-[4-(3,3-dimethyltriazol-1-yl)phenyl]-3-amino-4-S-(4-chlorobenzyl)-1,2,4-triazole (6g), 2-[4-(3,3-dimethyltriazol-1-yl)phenyl]-3-amino-4-S-(2,4-dichlorobenzyl)-1,2,4-triazole (6h), 2-[4-(3,3-methylbenzyltriazen-1-yl)-phenyl]-3-amino-4-S-benzyl-1,2,4-trioxazole (6i), 2-[4-(3,3-methylbenzyltriazen-1-yl)phenyl]-3-amino-4-S-(4-methylbenzyl)-1,2,4-triazole (6j), 2-[4-(3,3-methylbenzyltriazen-1-yl)phenyl]-3-amino-4-S-(4-methoxybenzyl)-1,2,4-triazole (6l), 2-[4-(3,3-methylbenzyltriazen-1-yl)phenyl]-3-amino-4-S-(2,4-di-chlorobenzyl)-1,2,4-triazole (6p) exhibited good anti-cancer activity against J82 cells with the IC₅₀ values of 23.883, 5.512, 8.731, 8.077, 5.590 and 12.195 μmol/L, respectively. And compounds 6h, 6i, 6j, 6l exhibited good anti-cancer activity against DU145 cells with the IC₅₀ values of 13.690, 21.908, 10.772 and 4.827 μmol/L, respectively.
Key words: triazene, 1,2,4-triazole, synthesis, antitumor


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