Citation: LIU Changhui, WEN Ruiming, HE Miao, YI Xianwen, YE Xiaoqin, FANG Lei. Synthesis and Antitumor Activities of Novel Thiosemicarbazone Derivatives with Ionone-Based Bischalcone[J]. Chinese Journal of Applied Chemistry, ;2017, 34(8): 899-904. doi: 10.11944/j.issn.1000-0518.2017.08.170022 shu

Synthesis and Antitumor Activities of Novel Thiosemicarbazone Derivatives with Ionone-Based Bischalcone

College of Chemistry and Environmental Engineering, Hu'nan City University, Yiyang, Hu'nan 413000, China

Corresponding author: LIU Changhui, changzi915@126.com
Received Date: 20 January 2017
Revised Date: 27 February 2017
Accepted Date: 28 April 2017

Fund Project: the Research Foundation of Education Bureau of Hu′nan Province, China No.15B043Supported by the Research Foundation of Education Bureau of Hu′nan Province, China(No.15B043), the Planned Science and Technology Project of Hu′nan Province, China(2009SK4027)the Planned Science and Technology Project of Hu′nan Province, China 2009SK4027

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In this work, a variety of new thiosemicarbazone derivatives were prepared by combining ionoe with chalcone and thiosemicarbazide according to the structure-activity combination principle. The ionone-based dichalcones were firstly synthesized through the condensation of ionone and substituted benzaldehydes, followed by thiosemicarbazide to obtain the target products. Their structures were confirmed by fourier transform infrared spectroscopy(FT-IR), nuclear magnetic resonance spectroscopy(¹H NMR and ¹³C NMR), elemental analysis, and mass spectrometry(MS). The in vitro antitumor activities against MCF-7(human breast cancer), HepG2(human liver cancer) and A549(human lung cancer) cells were tested using a 3-(4, 5-dimethyl-2-thiazolyl)-2, 5-diphenyl-2-H-tetrazolium bromide(MTT) method. The bioassay results demonstrate that compounds 3a and 3b display highly effective antiproliferative effects against MCF-7 cells with half maximal inhibitory concentration(IC₅₀) values of 10.83 and 7.62 μmol/L, respectively. Compound 3e exhibits preferable antiproliferative activities against A549 cells with an IC₅₀ value of 13.36 μmol/L, while compound 3f shows the best inhibitory effect against HepG2 cells with an IC₅₀ value of 8.55 μmol/L. Antitumor experiments show that the activities of these compounds are mainly affected by ionone and substituted groups in aromatic rings of chalcone.
- thiosemicarbazone,
- chalcone,
- ionone,
- antitumor activity,
- synthesis
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