新型1,2,4-三唑三氮烯衍生物的合成及其生物活性
收稿日期: 2018-02-07
修回日期: 2018-03-31
网络出版日期: 2018-05-17
基金资助
国家自然科学基金（No.J1210060）、河南省科技攻关计划（No.0624420031）及河南省基础研究基金（No.022463001）资助项目.
Synthesis and Biological Activities of Novel 1,2,4-Triazole Triazene Derivatives
Received date: 2018-02-07
Revised date: 2018-03-31
Online published: 2018-05-17
Supported by
Project supported by the National Natural Science Foundation of China (No. J1210060), the Science and Technology Planning Project of Henan Province (No. 0624420031) and the Basic Research Development Program of Henan Province (No. 022463001).
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.
魏光璞 , 张茜 , 雷强 , 徐淼 , 张明千 , 龙跃 . 新型1,2,4-三唑三氮烯衍生物的合成及其生物活性[J]. 有机化学, 2018 , 38(8) : 2137 -2142 . DOI: 10.6023/cjoc201802013
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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