Synthesis and Biological Activities of Novel 1,2,4-Triazole Triazene Derivatives

doi:10.6023/cjoc201802013

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (8): 2137-2142.DOI: 10.6023/cjoc201802013 Previous Articles Next Articles

Notes

新型1,2,4-三唑三氮烯衍生物的合成及其生物活性

魏光璞, 张茜, 雷强, 徐淼, 张明千, 龙跃

郑州大学化学与分子工程学院郑州 450001

收稿日期:2018-02-07 修回日期:2018-03-31 发布日期:2018-05-17
通讯作者: 龙跃 E-mail:Correspondingauthor.longyue@zzu.edu.cn
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

Wei Guangpu, Zhang Xi, Lei Qiang, Xu Miao, Zhang Mingqian, Long Yue

College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001

Received:2018-02-07 Revised:2018-03-31 Published:2018-05-17
Contact: 10.6023/cjoc201802013 E-mail:Correspondingauthor.longyue@zzu.edu.cn
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).

1. Synthesis and Biological Activities of Novel 1,2,4-Triazole Triazene Derivatives.PDF(676KB)

Abstract

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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Wei Guangpu, Zhang Xi, Lei Qiang, Xu Miao, Zhang Mingqian, Long Yue. Synthesis and Biological Activities of Novel 1,2,4-Triazole Triazene Derivatives[J]. Chin. J. Org. Chem., 2018, 38(8): 2137-2142.

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新型1,2,4-三唑三氮烯衍生物的合成及其生物活性

Synthesis and Biological Activities of Novel 1,2,4-Triazole Triazene Derivatives

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