Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (4): 902-907.DOI: 10.6023/cjoc201612007 Previous Articles     Next Articles

ARTICLE

新型5,6-二氢-6-烷基吡喃酮类衍生物的设计、合成及肿瘤细胞增殖抑制活性研究

徐海伟b, 贾世龙a,b, 谢晓平b, 罗姣b, 王树a   

  1. a. 河北北方学院药学系 张家口 075000;
    b. 郑州大学药学院 郑州 450001
  • 收稿日期:2016-12-02 修回日期:2016-12-30 出版日期:2017-04-25 发布日期:2017-01-17
  • 通讯作者: 徐海伟, 王树 E-mail:xhwei01@126.com
  • 基金资助:

    河南省高校科技创新人才计划(No.14HASTIT0031)资助项目.

Design, Synthesis and Anti-proliferative Activity of Novel 5,6-Dihydro-6-alkyl-2-pyrone Analogues

Xu Haiweib, Jia Shilonga,b, Xie Xiaopingb, Luo Jiaob, Wang Shua   

  1. a. Department of Pharmacy, Hebei North University, Zhangjiakou 075000;
    b. School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou 450001
  • Received:2016-12-02 Revised:2016-12-30 Online:2017-04-25 Published:2017-01-17
  • Contact: 10.6023/cjoc201612007 E-mail:xhwei01@126.com
  • Supported by:

    Project supported by the Program for Science & Technology Innovation Talents of Henan Province (No. 14HASTIT0031).

In order to investigate whether the modification at the double bonds in the pyrone skeleton would affect their biological activity. Based on the 5,6-dihydro-6-alkyl-2-pyrone goniothalamin, a series of new compounds 5, 6 and 8 were designed and synthesized, which were obtained by modification at the unsubstituted double bonds. Their cell proliferation inhibition activities against human liver cancer (7721), human lung cancer (A549), human esophageal cancer (EC-109), human gastric cancer (MGC-803) cell lines were assessed by thiazolyl blue tetrazolium bromide (MTT) method. Most of synthetic compounds lost their bioactivities via a comparision with positive control but 6-(benzyloxy)methyl-3-methyl-4-(2,3,4,5-tetra- fluorobenzamine)-5,6-dihydro-2H-pyran-2-one (6d). The results indicate that the unsaturated double bond is a key functional group for the bioactivity of these compounds and it is possible to keep their anti-cancer proliferation activity and reduce their toxicity by modification of the unsaturated double bond in 5,6-dihydro-6-alkyl-2-pyrones.

Key words: α,β-unsaturated δ-lactone, synthesis, cancer, antiproliferative activity