Citation: 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 shu

Synthesis and Cytotoxic Activity of Novel Resveratrol-Chalcone Amide Derivatives

Gao Hui ^a,† ,
Zheng Xi ^b,† ,
Qi Yan ^b ,
Wang Si ^a ,
Wan Chunping ^b,, ,
Rao Gaoxiong ^a ,
Mao Zewei ^a,,

a.
College of Pharmaceutical Science, Yunnan University of Traditional Chinese Medicine, Kunming 650500
b.
Central laboratory, The NO.1 Affiliated Hospital of Yunnan University of Traditional Chinese Medicine, Kunming 650021

Corresponding author: Wan Chunping, wanchunping1012@163.com Mao Zewei, maozw@ynutcm.edu.cn
Received Date: 17 August 2017
Revised Date: 25 October 2017
Available Online: 17 March 2017
Fund Project: the Application Basic Research Program of Yunnan Province 2014FZ078Project 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))the Yunnan Provincial Science and Technology Department-Applied Basic Research Joint Special Funds of Yunnan University of Traditional Chinese Medicine 2017FF117（-023）the National Natural Science Foundation of China 81460624the National Natural Science Foundation of China 81560620

Figures(4)

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.
- resveratrol-chalcone,
- amide derivatives,
- synthesis,
- cytotoxic activity
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