Synthesis, electrochemistry and anticancer activity of novel ferrocenyl phenols prepared via azide-alkyne 1,3-cycloaddition reaction

A series of monophenols and diphenols containing the ferrocene-Ctriazolyl and ferrocene-Ntriazolyl bond were prepared in a cycloaddition reaction of ethynylferrocene with aryl and benzyl azides and in a reaction of azidoferrocene with phenylacetylenes, respectively. The anticancer activity of the prepared compounds against hormone-dependent (MCF-7) and hormone-independent (HCC38) breast cancer cell lines was studied. The investigated compounds exhibited moderate anticancer activity against hormone-independent (IC50 ∼ 15–48 μM) cancer cell line and low activity against hormone-dependent cancer cell line (IC50 ∼ 84–98 μM).

Synthesis of 1-ferrocenyl-4-(4-hydroxyphenyl)- and 4-ferrocenyl-1-(4-hydroxyphenyl)-1H-1,2,3-triazoles. Electrochemical properties of the synthesised compounds. Cytotoxic activities of the prepared compounds against hormone-dependent (MCF-7, IC50 ≈ 15–48 μM ) and hormone-independent (HCC38, IC50 ≈ 84–98 μM) cancer cell lines.Figure optionsDownload as PowerPoint slideHighlights
► Synthesis of two series of ferrocenyl 1H-1,2,3-triazoles via Huisgen cycloaddition reaction.
► C–H arylation of 1H-1,2,3-triazoles.
► Electrochemical properties of prepared compounds.
► Cytotoxicity of obtained compounds against human breast cancer cell lines.
► The lowest IC50 of 15.3 μM has been found for the 4-ferrocenyl-1-(4-hydroxyphenyl)-1H-1,2,3-triazole.