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

作者：Xu, Haiwei^*; Jia, Shilong; Xie, Xiaoping; Luo, Jiao; Wang, Shu^*

来源：Chinese Journal of Organic Chemistry, 2017, 37(4): 902-907.

DOI：10.6023/cjoc201612007

• alpha,beta-unsaturated delta-lactone
• synthesis
• cancer
• antiproliferative activity

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-tetrafluorobenzamine)- 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.

• 出版日期2017-4-25
• 单位河北北方学院; 郑州大学