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Open AccessArticle

Synthesis and In Vitro Anticancer Evaluation of Novel Chrysin and 7-Aminochrysin Derivatives

1
Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, Gellért tér 4, H-1111 Budapest, Hungary
2
Medicinal Chemistry Research Group, Institute of Organic Chemistry, Research Centre for Natural Sciences, Magyar tudósok krt. 2, H-1117 Budapest, Hungary
3
Spectroscopic Research Department, Gedeon Richter Plc., P.O. Box 27, H-1475 Budapest, Hungary
*
Authors to whom correspondence should be addressed.
Molecules 2020, 25(4), 888; https://doi.org/10.3390/molecules25040888
Received: 27 January 2020 / Revised: 13 February 2020 / Accepted: 13 February 2020 / Published: 17 February 2020
(This article belongs to the Collection Natural Products: Anticancer Potential and Beyond)
Chrysin is a naturally occurring flavonoid with mild anticancer activity. In this paper we report the synthesis of new chrysin derivatives alkylated with N-phenylchloroacetamides in position 7. A novel method was developed for the preparation of 7-aminochrysin derivatives via the Smiles rearrangement, resulting in diphenylamine-type compounds. In silico studies of the Smiles rearrangement were performed. We also present the in vitro antiproliferative activity of the synthesized compounds against 60 human tumor cell lines (NCI60). The most potent derivative exhibited nanomolar antitumor activity on the MCF7 cell line of breast cancer (GI50 = 30 nM) and on the HCT-15 cell line of colon cancer (GI50 = 60 nM). View Full-Text
Keywords: flavonoid; chrysin; aminoflavonoid; anticancer activity; Smiles rearrangement flavonoid; chrysin; aminoflavonoid; anticancer activity; Smiles rearrangement
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MDPI and ACS Style

Mayer, S.; Keglevich, P.; Ábrányi-Balogh, P.; Szigetvári, Á.; Dékány, M.; Szántay, C., Jr.; Hazai, L. Synthesis and In Vitro Anticancer Evaluation of Novel Chrysin and 7-Aminochrysin Derivatives. Molecules 2020, 25, 888.

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