Synthesis and Antitumor Activities of Disulfide Derivatives Containing 1,3,4-Thiadiazole Moiety

doi:10.6023/cjoc201505027

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (12): 2624-2628.DOI: 10.6023/cjoc201505027 Previous Articles Next Articles

Notes

含1,3,4-噻二唑的二硫醚衍生物的合成及抗肿瘤活性研究

李莎, 荆芬, 付小云, 赵继军, 王雪峰, 李宝林, 刘玉明, 陈宝泉

天津理工大学化学化工学院天津 300384

收稿日期:2015-05-16 修回日期:2015-07-12 发布日期:2015-08-31
通讯作者: 陈宝泉 E-mail:chenbaoquan66@126.com
基金资助:
国家自然科学基金(No. 20971097)和天津市自然科学基金(No. 13JCYBJC24500)资助项目.

Synthesis and Antitumor Activities of Disulfide Derivatives Containing 1,3,4-Thiadiazole Moiety

Li Sha, Jing Fen, Fu Xiaoyun, Zhao Jijun, Wang Xuefeng, Li Baolin, Liu Yuming, Chen Baoquan

School of Chemistry and Chemical Engineering, Tianjin University of Technology, Tianjin 300384

Received:2015-05-16 Revised:2015-07-12 Published:2015-08-31
Supported by:
Project supported by the National Natural Science Foundation of China (No. 20971097) and the Tianjin Municipal Natural Science Foundation (No. 13JCYBJC24500).

1. Synthesis and Antitumor Activities of Disulfide Derivatives Containing 1,3,4-Thiadiazole Moiety.PDF(291KB)

Abstract

Ten novel disulfide derivatives containing 1,3,4-thiadiazole moiety were synthesized from appropriate thiols, thiourea and 2-amino-5-mercapto-1,3,4-thiadiazole via two steps reactions. All compounds were characterized by IR,¹H NMR, ESI-MS techniques and elemental analysis. The in vitro antiproliferative activities of target compounds against SMMC-7721 (human liver cancer cell), MCF-7 (human breast cancer cell) and A549 (human lung cancer cell) cells were evaluated by CCK-8 assay. The bioassay results demonstrated that most of the tested compounds showed better antiproliferative activities, and exhibited stronger effects than positive control 5-fluorouracil (5-FU) against various cancer cell lines. Particularly, n-propyl (2-amino-1,3,4-thiadiazol-5-yl)disulfide (3b) and n-butyl (2-amino-1,3,4-thiadiazol-5-yl)disulfide (3d) displayed highly effective antiproliferative effects against SMMC-7721 cells with IC₅₀values of 1.68 and 1.93 μmol/L. 4-Chlorobenzyl (2-amino-1,3,4-thiadiazol-5-yl)disulfide (3i) exhibited significant antiproliferative activities against MCF-7 cells with IC₅₀value of 1.78 μmol/L, and revealed the best inhibitory effect against A549 cells with IC₅₀ value of 4.04 μmol/L.

Key words: 1,3,4-thiadiazole, disulfide, synthesis, antitumor activity

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Li Sha, Jing Fen, Fu Xiaoyun, Zhao Jijun, Wang Xuefeng, Li Baolin, Liu Yuming, Chen Baoquan. Synthesis and Antitumor Activities of Disulfide Derivatives Containing 1,3,4-Thiadiazole Moiety[J]. Chin. J. Org. Chem., 2015, 35(12): 2624-2628.

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含1,3,4-噻二唑的二硫醚衍生物的合成及抗肿瘤活性研究

Synthesis and Antitumor Activities of Disulfide Derivatives Containing 1,3,4-Thiadiazole Moiety

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