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2019 , Vol. 39 >Issue 11: 3283 - 3288

DOI: https://doi.org/10.6023/cjoc201905035

研究简报

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 ,
  • 张明千 ,
  • 李子秋 ,
  • 罗德福 ,
  • 李龙辉 ,
  • 俞婷婷 ,
  • 龙跃
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  • 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

  网络出版日期: 2019-07-17

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)

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

  • Yanjun Chen ,
  • Mingqian Zhang ,
  • Ziqiu Li ,
  • Defu Luo ,
  • Longhui Li ,
  • Tingting Yu ,
  • Yue Long
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  • 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 date: 2019-05-14

  Online published: 2019-07-17

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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摘要

把三氮烯结构与1，3，4-噻二唑、酰胺相拼接，合成了14个未见报道的1，3，4-噻二唑三氮烯酰胺衍生物，并用核磁共振谱（NMR）、红外光谱（IR）和高分辨质谱（HRMS）等方法对化合物结构进行表征.通过以典型三氮烯药物达卡巴嗪作参照，对人食管癌细胞（EC109）、人胃癌细胞（MGC803）和人前列腺癌细胞（PC-3）做活性检测，结果显示化合物8a，8h，8i，8k，8l对人前列腺癌细胞（PC-3）的抑制活性最好，其IC50值分别为33.02，34.05，7.71，4.82，23.84μmol·L-1，远低于对照药达卡巴嗪（IC50值为146.43 μmol·L-1）.

关键词： 三氮烯; 1, 3, 4-噻二唑; 酰胺; 人食管癌细胞; 人胃癌细胞; 人前列腺癌细胞

本文引用格式

陈彦君 , 张明千 , 李子秋 , 罗德福 , 李龙辉 , 俞婷婷 , 龙跃 . 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[J]. 有机化学, 2019 , 39(11) : 3283 -3288 . DOI: 10.6023/cjoc201905035

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

参考文献

[1] Carvalho E. Francisco A. P. Iley J. Rosa E. Bioorg. Med. Chem. 2000 8 1719.
[2] Lei Q. Zhang S. Y. Liu M. L. Li J. Zhang X. Long Y. Mol. Divers. 2017 21 957.
[3] Wei G. P. Zhang X. Lei Q. Xu M. Zhang M. Q. Long Y. Chin. J. Org. Chem. 2018 38 2137.
[3] 魏 光璞 张 茜 雷 强 徐 淼 张 明千 龙 跃 有机化学 2018 38 2137.
[4] Carvalho E. Francisco A. P. Iley J. Rosa E. Bioorg. Med. Chem. 2000 8 1719.
[5] Wan J. L. Wu S. Q. Gan Y. Y. Meng J. Wang Z. C. Ouyang G. P. Chem. J. Chin. Univ. 2018 39 1683.
[5] 万 金林 巫 受群 甘 宜远 孟 娇 王 贞超 欧阳 贵平 高等学校化学学报 2018 39 1683.
[6] Flefel E. M. El-Sayed W. A. Mohamed A. M. El-Sofany W. I. Awad H. M. Molecules 2017 22 170.
[7] Martinez A. Alonso D. Castro A. Aran V. J. Cardelus I. Banos E. Arch. Pharm. 2010 332 191.
[8] Foroumadi A. Emami S. Hassanzadeh A. Rajaee M. Sokhanvar K. Moshafi M. H. Bioorg. Med. Chem. Lett. 2005 15 4488.
[9] Wei Q. Y. Wang X. M. Cheng J. H. Zeng G. X. Sun D. W. Food Chem. 2018 268 220.
[10] Buysse A. M. Yap M. C. H. Hunter R Babcock J. Huang X. P. Pest Manage. Sci. 2017 73 782.
[11] Heller L. Knorrscheidt A. Flemming F. Wiemann J. Sommerwerk S. Pavel L. Z. Al-Harrasi A. Csuk R. Bioorg. Chem. 2016 68 137.
[12] Zheng Y. G. Guo J. J. Yu Z. L. Fu R. K. Huang Y. Wang Y. H. Deng Z. Wu Y. Fine Chem. Intermed. 2015 45 1.
[12] 郑 玉国 郭 晴晴 余 忠林 付 如凯 黄 勇 王 永欢 邓 钊 吴 用 精细化工中间体 2015 45 1.
[13] Ruan X. H. Zhao H. J. Zhang C. Chen L. J. Li P. Wang Y. H. He M. Xue W. Chem. J. Chin. Univ. 2018 39 1197.
[13] 阮 祥辉 赵 洪菊 张 橙 陈 丽娟 李 普 王 一会 贺 鸣 薛 伟 高等学校化学学报 2018 39 1197.
[14] Zhang M. Q. Liu B. K. Lei Q. Yan J. D. Zhao Z. Y. Long Y. Chin. J. Org. Chem. 2019 39 1064.
[14] 张 明千 刘 斌凯 雷 强 颜 景东 赵 中玉 龙 跃 有机化学 2019 39 1064.
[15] Liu W. W. Liu X. J. Yin L. Cheng F. C. Chem. Bull. 2016 79 929.
[15] 刘 玮炜 刘 秀坚 殷 龙 程 峰昌 化学通报 2016 79 929.
[16] Hu H. X. Yang L. Y. Wu X. Cai X. T. Yan X. Y. Kong L. C. J. Zhejiang Normal Univ. (Nat. Sci.) 2018 41 416.
[16] 胡 鸿雨 杨 丽媛 吴 鑫 蔡 旭婷 严 晓阳 孔 黎春 浙江师范大学学报(自然科学版) 2018 41 416.
[17] Mao Z. W. Liu B. Zhu P. Zhang L. J. Zhu J. H. Wu L. Z. Wan C. P. Chin. J. Org. Chem. 2018 38 2167.
[17] 毛 泽伟 刘 蓓 朱 萍 张 丽君 朱 加洪 伍 林泽 万 春平 有机化学 2018 38 2167.
[18] Farquhar D. Benvenuto J. J. Med. Chem. 1984 27 1723.
[19] Giraldi T. Nisi C. J. Med. Chem. 1977 20 850.
[20] Trapero A. Pacitto A. Singh V. Sabbah M. Coyne A. G. Mizrahi V. Blundell T. L. Ascher D. B. Abel C. J. Med. Chem. 2018 61 2806.
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