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

Autor: Mernyák, Erzsébet, Bartha, Sándor, Kóczán, Lili, Jójárt, Rebeka, Resch, Vivien, Paragi, Gábor, Vágvölgyi, Máté, Hunyadi, Attila, Bruszel, Bella, Zupkó, István, Minorics, Renáta
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Zdroj: Journal of Enzyme Inhibition & Medicinal Chemistry; Dec2021, Vol. 36 Issue 1, p1931-1937, 7p
Abstrakt: Microwave-assisted phospha-Michael addition reactions were carried out in the 13α-oestrone series. The exocyclic 16-methylene-17-ketones as α,β-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 16α-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-13α-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. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index
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