Chinese Journal of Organic Chemistry >
Synthesis and Cytotoxic Activity of Novel Resveratrol-Chalcone Amide Derivatives
Received date: 2017-08-17
Revised date: 2017-10-25
Online published: 2017-11-17
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 81560620, 81460624), the Application Basic Research Program of Yunnan Province (No. 2014FZ078) and the Yunnan Provincial Science and Technology Department-Applied Basic Research Joint Special Funds of Yunnan University of Traditional Chinese Medicine (No. 2017FF117(-023)).
Resveratrol is a type of natural phenol with a broad range of good biological activities. Based on former work, in order to look for new anticancer agents, a series of novel amide compounds between resveratrol and chalcone possessing piperazine moiety have been synthesized by connecting principle of active biological groups. The structures of compounds were characterized by IR, 1H NMR, 13C NMR and HRMS, and in vitro cytotoxic activity was evaluated against a panel of human tumor cell lines (Hela, A549 and SGC7901) by the 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay. The results demonstrated that amide compounds contributed good cytotoxic activity. Especially, (E)-3-(2,4-dimethoxy-6-((E)-4-methoxystyryl)phenyl)-1-(4-(N-acryloyl)piperazin-1-yl)phenylprop-2-en-1-one (9) showed the best cytotoxic activity against A549 and Hela (IC50=0.26 and 7.35 μmol·L-1, respectively), and fluorescence-activated cell sorter (FACs) analysis showed that compound 9 significantly induced apoptosis in A549 cell.
Key words： resveratrol-chalcone; amide derivatives; synthesis; cytotoxic activity
Gao Hui , Zheng Xi , Qi Yan , Wang Si , Wan Chunping , Rao Gaoxiong , Mao Zewei . Synthesis and Cytotoxic Activity of Novel Resveratrol-Chalcone Amide Derivatives[J]. Chinese Journal of Organic Chemistry, 2018 , 38(3) : 648 -655 . DOI: 10.6023/cjoc201708031
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