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



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   

  1. 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;
  • 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 Xiaohuia, Yan Defenga, Ma Kedonga, He Lingshuanga, Gao Ruiqia, Xu Yaozhongb, Li Depenga   

  1. 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