Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (2): 439-445.DOI: 10.6023/cjoc201409008 Previous Articles     Next Articles



魏梦雪a, 高晓慧a, 张和a, 李学强a,b   

  1. a 宁夏大学化学化工学院 银川 750021;
    b 宁夏天然药物工程技术研究中心 银川 750021
  • 收稿日期:2014-09-05 修回日期:2014-10-01 发布日期:2014-10-21
  • 通讯作者: 李学强
  • 基金资助:

    国家自然科学基金(Nos. 21462032、21062014)、宁夏大学人才引进科研启动基金(No. 80020241)和宁夏大学“211”工程建设(No. ndzr09-1)资助项目.

Synthesis of New Chiral γ-Alkoxy-2(5H)-furanone-piperazine-sulfonamide Compounds and Preliminary Evaluation of in Vitro Anticancer Activity

Wei Mengxuea, Gao Xiaohuia, Zhang Hea, Li Xueqianga,b   

  1. a School of Chemistry and Chemical Engineering, Ningxia University, Yinchuan 750021;
    b Ningxia Engineering Research Center for Natural Medicines, Yinchuan 750021
  • Received:2014-09-05 Revised:2014-10-01 Published:2014-10-21
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21462032, 21062014), the Research Starting Funds for Imported Talents of Ningxia University (No. 80020241), and the “211” Project in Ningxia University (No. ndzr09-1).

The enantiomerically pure 5-(S)-5-alkoxy-3,4-dibromo-2(5H)-furanones were readily prepared from furfural through a three-step sequence of bromine-promoted oxidation/acetalization of mucobromic acid with chiral (-)-menthol and (+)-borneol/recrystallization of the resulting γ-butenolides. Then the chiral γ-butenolides were reacted with piperazine through a one-pot two-step protocol combining Michael addition and elimination of hydrogen bromide, resulting in the crude furanone-piperazines, which were further toslated with a range of sulfonyl chlorides. 12 furanone-piperazine-sulfonamide complexs were efficiently obtained in moderate to excellent yields (45.3%~96.2%). All the new compounds were identified by 1H NMR, 13C NMR, IR and HRMS technology. The in vitro anti-tumor activities of these complexs against cervical cancer cell lines (Hela) were evaluated by thiazolylblue (MTT) assay method. Among them, 5-(S)-5-borneolyloxy-4-(p-nitrobenzene-sulfonamide-piperazinyl)-3-bromo-2(5H)-furanone (7k) exhibited the best inhibitory activity with an IC50 of 0.02 μmol/L, providing a new promising lead for further development of new anti-Hela drugs.

Key words: butenolide, furanone-piperazine-sulfonamide, synthesis, Hela cells, anti-tumor activity