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有机化学 ›› 2020, Vol. 40 ›› Issue (1): 221-225.DOI: 10.6023/cjoc201907054 上一篇    下一篇

研究简报

5-卤代-2'-脱氧-2'-β-氟-4'-叠氮嘧啶核苷的合成与抗乙肝病毒活性研究

郭美超a, 康进峰a, 侯姣a, 张倩倩a, 于文全a, 常俊标a,b   

  1. a 郑州大学化学学院 郑州 450001;
    b 河南师范大学化学化工学院 河南省有机功能分子和药物创新重点实验室 河南新乡 453007
  • 收稿日期:2019-07-30 修回日期:2019-09-09 发布日期:2019-09-18
  • 通讯作者: 于文全, 常俊标 E-mail:wenquan_yu@zzu.edu.cn;changjunbiao@zzu.edu.cn
  • 基金资助:
    国家自然科学基金（Nos.81773570，U1804283）和郑州大学青年骨干教师基金（No.2017ZDGGJS020）资助项目.

Synthesis and Anti-HBV Evaluation of 5-Halogenated 2'-Deoxy-2'-β-fluoro-4'-azido Pyrimidine Nucleosides

Guo Meichaoa, Kang Jinfenga, Hou Jiaoa, Zhang Qianqiana, Yu Wenquana, Chang Junbiaoa,b   

  1. a College of Chemistry, Zhengzhou University, Zhengzhou 450001;
    b Henan Key Laboratory of Organic Functional Molecules and Drug Innovation, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, He'nan 453007
  • Received:2019-07-30 Revised:2019-09-09 Published:2019-09-18
  • Supported by:
    Project supported by the National Natural Science Foundation of China (Nos. 81773570, U1804283) and the Young Backbone Teachers Fund of Zhengzhou University (No. 2017ZDGGJS020).

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补充材料

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以（间氯）苯甲酰基保护的2'-脱氧-2'-β-氟-4'-叠氮尿苷为起始原料，经过硝酸铈铵（CAN）介导的卤代、三氮唑活化、胺化、脱保护合成了一系列5-卤代的2'-脱氧-2'-β-氟-4'-叠氮嘧啶核苷类化合物.体外生物活性评价研究表明，5-氯代（6a）和5-碘代（6c）核苷衍生物具有很好的抗乙肝病毒活性，而且细胞毒性较小.

关键词: 5-卤代, 嘧啶核苷, 合成, 抗乙肝病毒活性

A series of 5-halogenated 2'-deoxy-2'-β-fluoro-4'-azido pyrimidine nucleosides were synthesized from m-chloro-benzoyl protected 2'-deoxy-2'-β-fluoro-4'-azido uridine via ammonium cerium nitrate (CAN)-mediated halogenation, activation by triazole, amination, and deprotection. In vitro biological evaluation demonstrated that 5-chloro (6a) and 5-iodo (6c) nucleoside derivatives possess potent anti-HBV (hepatitis B virus) activity with low cytotoxicity.

Key words: 5-halogenated, pyrimidine nucleoside, synthesis, anti-HBV activity