Synthesis and In Vitro Anticancer Evaluation of Chrysin Containing Hybrids and Other Chrysin Derivatives

Authors

  • Szabolcs Mayer
    Affiliation
    Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, Műegyetem rkp. 3., H-1111 Budapest, Hungary
  • Dominika Mária Herr
    Affiliation
    Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, Műegyetem rkp. 3., H-1111 Budapest, Hungary
  • Nóra Nagy
    Affiliation
    Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, Műegyetem rkp. 3., H-1111 Budapest, Hungary
  • Viktória Donkó-Tóth
    Affiliation
    Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, Műegyetem rkp. 3., H-1111 Budapest, Hungary
  • Péter Keglevich
    Affiliation
    Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, Műegyetem rkp. 3., H-1111 Budapest, Hungary
  • Márton Weber
    Affiliation
    Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, Műegyetem rkp. 3., H-1111 Budapest, Hungary Spectroscopic Research Department, Gedeon Richter Plc., H-1475 Budapest, P.O.B. 27, Hungary
  • Miklós Dékány
    Affiliation
    Spectroscopic Research Department, Gedeon Richter Plc., H-1475 Budapest, P.O.B. 27, Hungary
  • László Hazai
    Affiliation
    Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, Műegyetem rkp. 3., H-1111 Budapest, Hungary
https://doi.org/10.3311/PPch.21919

Abstract

Chrysin, a well-known naturally occurring flavonoid having several biological effects including antiproliferative activity, was coupled with different pharmacophore structures. Coupling was carried out with spacers of different lengths and types. Structures selected for hybrid formation were amines, cyclic amino acid esters, and (hetero)aromatic compounds. In addition, vindoline, which is a Vinca alkaloid containing an indole skeleton, was also used. The alkylation of amines in the presence of carbonate base resulted in an interesting carbamate side product formation beside the expected amine. We also present the detailed structure elucidation of the carbamates. The in vitro anticancer activities of the synthesized derivatives were examined against 60 human tumor cell lines in National Cancer Institute (NCI, USA).

Keywords:

chrysin, flavonoid, vindoline, heterocycles, anticancer effet

Citation data from Crossref and Scopus

Published Online

2023-05-23

How to Cite

Mayer, S., Herr, D. M., Nagy, N., Donkó-Tóth, V., Keglevich, P., Weber, M. “Synthesis and In Vitro Anticancer Evaluation of Chrysin Containing Hybrids and Other Chrysin Derivatives”, Periodica Polytechnica Chemical Engineering, 67(2), pp. 316–336, 2023. https://doi.org/10.3311/PPch.21919

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Articles