有机化学 ›› 2023, Vol. 43 ›› Issue (9): 3167-3173.DOI: 10.6023/cjoc202303015 上一篇    下一篇

研究论文

新型2,2'-缩水-L-苏糖嘧啶膦酸核苷的合成

朱传涛a, 王松a, 赵一凡a, Herdewijn Pieta,c,*(), 刘丰五a,b,*()   

  1. a 郑州大学药物研究院 XNA生物医学研究所 郑州 450001
    b 郑州大学药物关键制备技术教育部重点实验室 郑州 450001
    c Medicinal Chemistry, Rega Institute for Medical Research, KU Leuven, Herestraat 49, 3000 Leuven, Belgium
  • 收稿日期:2023-03-10 修回日期:2023-05-05 发布日期:2023-06-13

Synthesis of Novel 2,2'-Anhydro-L-threosylpyrimidine Phosphonates

Chuantao Zhua, Song Wanga, Yifan Zhaoa, Piet Herdewijna,c(), Fengwu Liua,b()   

  1. a XNA Platform, Institute of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou 450001
    b Key Laboratory of Advanced Drug Preparation Technologies, Ministry of Education, Zhengzhou University, Zhengzhou 450001
    c Medicinal Chemistry, Rega Institute for Medical Research, KU Leuven, Herestraat 49, 3000, Leuven
  • Received:2023-03-10 Revised:2023-05-05 Published:2023-06-13
  • Contact: E-mail: fwliu@zzu.edu.cn;piet.herdewijn@kuleuven.be

首先通过九步反应合成了一系列L-苏糖嘧啶核苷膦酸酯. 用二乙胺基三氟化硫(DAST)处理L-苏糖嘧啶核苷膦酸酯, 分别以中高收率得到相应的2,2'-缩水-1-(L-苏糖)尿嘧啶核苷膦酸酯类似物. 对所得到的L-苏糖嘧啶核苷膦酸酯和2,2'-缩水-L-苏糖嘧啶膦酸核苷进行了初步的生物学评价, 未发现任何活性.

关键词: 2,2'-缩水核苷, 二乙胺基三氟化硫(DAST), L-苏糖嘧啶膦酸酯

A series of L-threoylnucleoside phosphonates were synthesized via a nine-step procedure firstly. When the L-threoylpyrimidine nucleoside phosphonate was treated by diethylaminosulphur trifluoride (DAST), all the tried pyrimidine L-threosylnucleoside phosphonate analogues produced corresponding 2,2'-anhydro-1-(L-threoyl)pyrimidine phosphonates in medium-high yields. The obtained L-threoylpyrimidine nucleoside phosphonates and 2,2'-anhydro-L-threosylpyrimidine phosphonic acids have not shown any activity by primary biological evaluations.

Key words: 2,2'-anhydronucleoside, diethylaminosulphur trifluoride (DAST), L-threosylpyrimidine phosphonate