Abstract:

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.

Key words: thiosemicarbazone, chalcone, ionone, antitumor activity, synthesis