Synthesis and Antitumor Activities of 1, 3, 4-Thiadiazole Triazene Amide Derivatives

doi:10.6023/cjoc201905035

Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (11): 3283-3288.DOI: 10.6023/cjoc201905035 Previous Articles Next Articles

1, 3, 4-噻二唑三氮烯酰胺衍生物的合成及抗肿瘤活性研究

陈彦君^a, 张明千^b, 李子秋^b, 罗德福^b, 李龙辉^b, 俞婷婷^c, 龙跃^b*()

^a焦作大学化学与环境工程学院河南焦作 454003
^b 郑州大学化学与分子工程学院郑州 450001
^c 郑州大学药学院郑州 450001

收稿日期:2019-05-14 发布日期:2019-07-17
通讯作者: 龙跃 E-mail:longyue@zzu.edu.cn
基金资助:
国家自然科学基金(J1210060);河南省科技攻关计划(0624420031);河南省基础研究基金(022463001)

Synthesis and Antitumor Activities of 1, 3, 4-Thiadiazole Triazene Amide Derivatives

Chen Yanjun^a, Zhang Mingqian^b, Li Ziqiu^b, Luo Defu^b, Li Longhui^b, Yu Tingting^c, Long Yue^b*()

^a Department of Chemical and Environmental Engineering, Jiaozuo Universiy, Jiaozuo, Henan 454003
^b College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001
^c School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou 450001

Received:2019-05-14 Published:2019-07-17
Contact: Long Yue E-mail:longyue@zzu.edu.cn
Supported by:
the National Natural Science Foundation of China(J1210060);the Science and Technology Planning Project of Henan Province(0624420031);the Basic Research Development Program of Henan Province(022463001)

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Abstract

By splicing the triazene structure with 1, 3, 4-thiadiazole and amide, fourteen unreported 1, 3, 4-thiadiazole triazene amide derivatives were synthesized. The structures of these compounds were characterized by nuclear magnetic resonance (NMR), infrared spectroscopy (IR) and high-resolution mass spectrometry (HRMS). By using the typical triazene drug dacarbazine as a reference, the activity detections of human esophageal cancer cells (EC109), human gastric cancer cells (MGC803) and human prostate cancer cells (PC-3) were carried out. The results showed that compounds 8a, 8h, 8i, 8k, and 8l had the best inhibitory activity against human prostate cancer cells (PC-3). And their IC₅₀ values were 33.02, 34.05, 7.71, 4.82, 23.84 μmol·L^-1, which were far lower than the control drug their IC₅₀ values were 33.02, 34.05, 7.71, 4.82, 23.84 μmol·L^-1, which were far lower than the control drug dacarbazine (146.43 μmol·L^-1).

Key words: triazene, ?, amide, human esophageal cancer cells, human gastric cancer cells, human prostate cancer cells

Cite this article

Chen Yanjun, Zhang Mingqian, Li Ziqiu, Luo Defu, Li Longhui, Yu Tingting, Long Yue. Synthesis and Antitumor Activities of 1, 3, 4-Thiadiazole Triazene Amide Derivatives[J]. Chinese Journal of Organic Chemistry, 2019, 39(11): 3283-3288.

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References 20

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Compd.	EC109	MGC803	PC-3
8a	＞300	＞300	33.02±1.85
8b	＞300	263.58±0.54	125.23±1.85
8c	＞300	179.24±1.17	＞300
8d	＞300	＞300	171.43±1.37
8e	＞300	277.53±0.54	152.79±1.04
8f	＞300	＞300	＞300
8g	＞300	＞300	＞300
8h	180.70±0.28	112.59±6.76	34.05±4.31
8i	215.94±5.26	197.83±1.00	7.71±0.06
8j	218.72±3.24	203.06±2.57	52.81±2.35
8k	57.17±2.90	90.77±3.20	4.82±0.71
8l	59.32±0.38	92.12±0.54	23.84±4.78
8m	205.28±7.17	280.58±3.06	84.36±2.28
8n	279.04±0.36	285.03±0.86	81.45±5.28
DTIC	108.1±1.2	99.6±4.1	146.4±5.1

Compd.	EC109	MGC803	PC-3
8a	＞300	＞300	33.02±1.85
8b	＞300	263.58±0.54	125.23±1.85
8c	＞300	179.24±1.17	＞300
8d	＞300	＞300	171.43±1.37
8e	＞300	277.53±0.54	152.79±1.04
8f	＞300	＞300	＞300
8g	＞300	＞300	＞300
8h	180.70±0.28	112.59±6.76	34.05±4.31
8i	215.94±5.26	197.83±1.00	7.71±0.06
8j	218.72±3.24	203.06±2.57	52.81±2.35
8k	57.17±2.90	90.77±3.20	4.82±0.71
8l	59.32±0.38	92.12±0.54	23.84±4.78
8m	205.28±7.17	280.58±3.06	84.36±2.28
8n	279.04±0.36	285.03±0.86	81.45±5.28
DTIC	108.1±1.2	99.6±4.1	146.4±5.1

1, 3, 4-噻二唑三氮烯酰胺衍生物的合成及抗肿瘤活性研究

Synthesis and Antitumor Activities of 1, 3, 4-Thiadiazole Triazene Amide Derivatives

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