Synthesis of novel cytotoxic 3-azolylsteroids via Cu-catalyzed C-N coupling

A series of novel 3-azolylandrosta-3,5-dienes was prepared via Cu-catalyzed Ullmann C-N coupling between a readily available steroidal vinyliodide and a variety of NH-heterocycles. The cytotoxic activity of the target compounds was evaluated against selected cancer cell lines (MCF-7, SKOV-3, DU-145, PC-3). Compound bearing gramine fragment showed the highest antiproliferative effect with IC50 values in the range of 2.0-10.1 mu M.