Microwave-assisted Phospha-Michael addition reactions in the 13α-oestrone series and in vitro antiproliferative properties

Mernyák, Erzsébet and Bartha, Sándor and Kóczán, Lili and Jójárt, Rebeka and Resch, Vivien and Paragi, Gábor and Vágvölgyi, Máté and Hunyadi, Attila and Bruszel, Bella and Zupkó, István and Minorics, Renáta (2021) Microwave-assisted Phospha-Michael addition reactions in the 13α-oestrone series and in vitro antiproliferative properties. JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 36 (1). pp. 1931-1937. ISSN 1475-6366

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Abstract

exocyclic 16-methylene-17-ketones as a,b-unsaturated ketones were reacted with secondary phosphine oxides as nucleophilic partners. The addition reactions furnished the two tertiary phosphine oxide diastereomers in high yields. The main product was the 16a-isomer. The antiproliferative activities of the newly synthesised organophosphorus compounds against a panel of nine human cancer cell lines were investigated by means of MTT assays. The most potent compound, the diphenylphosphine oxide derivative in the 3-O-methyl-13a-oestrone series (9), exerted selective cell growth-inhibitory activity against UPCI-SCC- 131 and T47D cell lines with low micromolar IC50 values. Moreover, it displayed good tumour selectivity property determined against non-cancerous mouse fibroblast cells.

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