Synthesis, characterization and anticancer evaluation of nitrogen-substituted 1-(3-aminoprop-1-ynyl)-4-hydroxyanthraquinone derivatives

Anthraquinones are of significant interest due to their biological activity, coloring properties, and synthetic applications. Here, we describe a mild convenient method for modification 1-ethynyl-4-hydroxyanthraquinone that was obtained from the Sonogashira cross-coupling reaction 1-hydroxy-4-iodoanthraquinone with alkynes. The copper(I) catalyzed one-pot three-component (A3-coupling) new secondary amines formaldehyde main approach synthesis nitrogen-substituted 1-[3-(amino)prop-1-ynyl]-4-hydroxyanthraquinones. influence different substituents in amine on rate yield has been evaluated. cytotoxicity 1-ethynyl-4-hydroxyanthraquinones assessed using conventional MTT assay. Among all compounds synthesized, anthraquinone-propargylamine derivatives 28, 29, 30, 34 possess most promising cytotoxic potential towards glioblastoma cancer cells; 14 19 shown selectivity prostate cells DU-145, 18, 24 — breast cell line MCF-7. grown inhibition these by 18 comparable those standard drug Doxorubicin. Molecular modeling anthraquinone DNA G-quadruplex binding sites performed help understand observed SAR trends.