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有机化学 ›› 2016, Vol. 36 ›› Issue (12): 2989-2996.DOI: 10.6023/cjoc201605026 上一篇    下一篇

研究简报

(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   

  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 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 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).

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以尿苷（1a）或2'-脱氧尿苷（1b）类化合物为原料，经碘代、选择性氧化、Heck反应等步骤快捷、环保地合成（E）-5-（2-溴乙烯基）尿苷/（E）-5-（2-溴乙烯基）-2'-脱氧尿苷（5a/5b），再通过酯化、硫羰基化、氨解等步骤合成新化合物（E）-4-硫-5-（2-溴乙烯基）尿苷/（E）-4-硫-5-（2-溴乙烯基）-2'-脱氧尿苷（8a/8b），共得到5种新的硫代产物，其中包含2种新产物8a/8b，3种新中间体7a，7b，10.其结构通过1H NMR，13C NMR，IR，UV，HRMS，X-Ray等谱图手段进行了表征.采用3-（4，5-二甲基-2-噻唑基）-2，5-二苯基-2H-溴化四唑（MTT）实验方法对8a及其类似物进行了细胞毒性评价，发现8a/8b是潜在的抗肿瘤药物.

关键词: (E)-4-硫-5-(2-溴乙烯基)尿苷, (E)-4-硫-5-(2-溴乙烯基)-2'-脱氧尿苷, 合成, 细胞毒性

(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