Synthesis of (E)-4-Thio-5-(2-bromovinyl)uridine/Deoxyuridine and Its Characterization and Cytotoxicity

doi:10.6023/cjoc201605026

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (12): 2989-2996.DOI: 10.6023/cjoc201605026 Previous Articles Next Articles

NOTE

(E)-4-硫-5-(2-溴乙烯基)尿苷/脱氧尿苷的合成及细胞毒性评价

张晓辉^a, 闫德峰^a, 马克东^a, 赫玲爽^a, 高瑞琦^a, 徐耀忠^b, 李德鹏^a

a 大连大学环境与化学工程学院大连 116622;
b 开放大学生命健康和化学科学学院英国

收稿日期:2016-05-16 修回日期:2016-07-08 发布日期:2016-08-12
通讯作者: 李德鹏, 闫德峰 E-mail:lidepeng@dlu.edu.cn;yandefeng1991@sina.com
基金资助:
辽宁省教育厅科技（No. L2013472）、大连市科技计划（No. 2014E12SF074）、大连市金州新区科技计划（No. KJCX-ZTP2014-0009）资助项目.

Synthesis of (E)-4-Thio-5-(2-bromovinyl)uridine/Deoxyuridine and Its Characterization and Cytotoxicity

Zhang Xiaohui^a, Yan Defeng^a, Ma Kedong^a, He Lingshuang^a, Gao Ruiqi^a, Xu Yaozhong^b, Li Depeng^a

a College of Environment and Chemical Engineering, Dalian University, Dalian 116622;
b Department of Life, Health and Chemical Sciences, the Open University, UK

Received:2016-05-16 Revised:2016-07-08 Published:2016-08-12
Supported by:
Project Supported by the Science and Technology Project of Liaoning Provincial Department of Education (No. L2013472), the Science-technology Plan Projects of Dalian Government (No. 2014E12SF074), the Science-technology Plan Projects of Dalian Jinzhou New Area Government (No. KJCX-ZTPY-2014-0009).

(E)-4-Thio-5-(2-brominevinyl)uridine/2'-deoxyuridine (8a/8b) were efficiently synthesized in an environmental friendly way from uridine/2'-deoxyuridine (1a/1b) that were first transformed to (E)-(2-brominevinyl)uridine/2'-deoxyuridine (5a/5b) via iodination, selective oxidation, and Heck reaction steps. The resulting products 5a/5b were then converted to the targets 8a/8b through esterification, thio-reaction of carbonyl, and hydrolysis steps. Two new compounds 8a/8b and three new intermediates 7a, 7b, 10 were obtained, and their structures have been fully characterized by ¹H NMR, ¹³C NMR, IR, UV, HR-MS and X-Ray. The study of 8a and their derivatives regarding cytotoxicity was carried out by using 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) experiment method, and the initial findings suggest that (E)-4-thio-5-(2-brominevinyl)uridine/2'-deoxyuridine (8a/8b) would be potential antitumor drugs.

Key words: (E)-4-thio-5-(2-bromovinyl)-uridine, (E)-4-thio-5-(2-bromovinyl)-2'-deoxyuridine, synthesis, cytotoxicity

Cite this article

Zhang Xiaohui, Yan Defeng, Ma Kedong, He Lingshuang, Gao Ruiqi, Xu Yaozhong, Li Depeng. Synthesis of (E)-4-Thio-5-(2-bromovinyl)uridine/Deoxyuridine and Its Characterization and Cytotoxicity[J]. Chin. J. Org. Chem., 2016, 36(12): 2989-2996.

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(E)-4-硫-5-(2-溴乙烯基)尿苷/脱氧尿苷的合成及细胞毒性评价

Synthesis of (E)-4-Thio-5-(2-bromovinyl)uridine/Deoxyuridine and Its Characterization and Cytotoxicity

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