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Synthesis and antiproliferative activity of aminoalkylated chalcones on three human cancer cells

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Abstract

Two series of 16 novel aminoalkylated chalcone derivatives 2a–h and 3a–h were synthesized from 2′-hydroxy-3,4,4′,6′-tetramethoxychalcone (1) through extending alkoxy side chain at the 2′-position, and introducting amine hydrogen bond receptor at the end of the side chain. Their in vitro antiproliferative activities were evaluated on a panel of three human cell lines (Hela, HCC1954, and SK-OV-3) by CCK-8 assay. The results showed that all the target compounds, except compound 3e, exhibited moderate to potent antiproliferative activities against these three human cancer cells with the IC50 values of 6.78–64.45 μmol/L, in particular compounds 2g (on Hela cells), 2c (on HCC1954 cells), and 2c, 2d (on SK-OV-3 cells) possess IC50 values below 10 μmol/L. It showed the introduction of aminoalkyl moiety at 2′-O-position of chalcone 1 resulted to produce the desired effect of increasing the antiproliferative activities, and the distance between the amino groups and chalcone moiety plays an important role, the optimal number of methylene units is two-carbon spacer.

Graphical abstract

A series of 16 novel aminoalkylated chalcones were synthesized and their antiproliferative acivities on three human cancer cells were evaluated.

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Acknowledgements

We thank the National Natural Science Foundation of China (No. J1210040) and Education Department of Hubei Province Science and Technology Research Project of China (No. Q20162803) for the financial support.

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Authors and Affiliations

  1. College of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082, China

    Cui Li, Xueli Li & Qiuan Wang

  2. School of Nuclear Technology and Chemistry & Biology, Hubei University of Science and Technology, Hubei, 437100, China

    Gangqiang Wang

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  1. Cui Li
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  2. Gangqiang Wang
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  3. Xueli Li
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  4. Qiuan Wang
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Correspondence to Qiuan Wang.

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Li, C., Wang, G., Li, X. et al. Synthesis and antiproliferative activity of aminoalkylated chalcones on three human cancer cells. Med Chem Res 27, 972–979 (2018). https://doi.org/10.1007/s00044-017-2120-6

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  • DOI: https://doi.org/10.1007/s00044-017-2120-6

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