Synthesis of a Novel Dual-Action Intermediate for the Chemotherapeutic Treatment of Prostate Cancer

Abstract

Prostate cancer affects more men in the United States than any other cancer with projections estimating that 220,800 men will be diagnosed in 2015. Advancements in drug design and research have substantially decreased the mortality of prostate cancers, however, the prevalence and incidence of the disease still displays the need for more effective treatments. A recently discovered class of molecules found in cruciferous vegetables, isothiocyanates (ITCs), has shown promise in treating prostate cancer cell lines, one of the molecules being phenethyl isothiocyanate (PEITC). It was noticed that enzalutamide, a drug used to treat castration resistant prostate cancer (CRPC), and PEITC have some similar structural features. A drug was rationally designed using the structures of PEITC and enzalutamide with the intent of working as a dual-action chemotherapeutic against prostate cancer. In this study, a critical intermediate, 4-(3-(6-(2-isothiocyanatoethyl) pyridin-3-yl)-4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl)-2-(trifluoromethyl) benzonitrile, was successfully synthesized providing a potential synthetic route the dual-action chemotherapeutic. We hypothesize the synthetic route offered by this study will yield success in the synthesis of a novel anti-prostate cancer drug.