Synthesis and Antiproliferative Activity of Thiadiazole Peptidomimetic Derivatives

doi:10.6023/cjoc201606017

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (12): 2895-2905.DOI: 10.6023/cjoc201606017 Previous Articles Next Articles

ARTICLE

噻二唑类肽衍生物的合成及抗肿瘤增殖活性研究

梁涛, 李嘉杰, 方金玉, 刘婷婷, 方浩

山东大学药学院济南 250012

收稿日期:2016-06-11 修回日期:2016-06-27 发布日期:2016-08-25
通讯作者: 方浩 E-mail:haofangcn@sdu.edu.cn
基金资助:
国家自然科学基金面上（No. 81373281）、山东省自然科学杰出青年基金（No. JQ201319）及国家级大学生创新创业训练计划（No. 10000072188007）资助项目.

Synthesis and Antiproliferative Activity of Thiadiazole Peptidomimetic Derivatives

Liang Tao, Li Jiajie, Fang Jinyu, Liu Tingting, Fang Hao

Department of Medicinal Chemistry, School of Pharmaceutical Sciences, Shandong University, Ji'nan 250012

Received:2016-06-11 Revised:2016-06-27 Published:2016-08-25
Supported by:
Project supported by the National Natural Science Foundation China (No. 81373281), the Shandong Natural Science Foundation for Distinguished Young Scholars (No. JQ201319) and the National College Students Foundation for Innovation and Entrepreneurship Training Program (No.10000072188007).

A series of thiadiazole peptidomimetic derivatives were prepared using different phenylacetic acids and thiosemicarbazide as the starting materials and followed by multi-step reactions. The structures of target compounds were identified by ¹H NMR, ¹³C NMR and HRMS. The preliminary biological evaluations were performed on chronic myelogenous leukemia cell (K562 cell) and prostatic cancer cell (PC-3 cell) with 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl tetrazolium bromide (MTT) assay. The results suggested that most of target compounds have good antiproliferative activities against K562 cell. Further evaluations focused on the five active compounds using three tumor cell lines and found that (S)-tert-butyl(1-((2-((5-([1,1'-biphenyl]-4-ylmethyl)-1,3,4-thiadiazol-2-yl)amino)-2-oxoethyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (6d) exhibited better antiproliferative activities against prostatic cancer cell (PC-3 cell) compared with AT-101.

Key words: thiadiazole peptidomimetic, antitumor activity, prostatic cancer cell

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Liang Tao, Li Jiajie, Fang Jinyu, Liu Tingting, Fang Hao. Synthesis and Antiproliferative Activity of Thiadiazole Peptidomimetic Derivatives[J]. Chin. J. Org. Chem., 2016, 36(12): 2895-2905.

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噻二唑类肽衍生物的合成及抗肿瘤增殖活性研究

Synthesis and Antiproliferative Activity of Thiadiazole Peptidomimetic Derivatives

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