Synthesis of geranylhydroquinone derivatives with potencial cytotoxic activity

natural geranylhydroquinone 1 and geranyl-p-methoxyphenol 2 were prepared by electrophilic aromatic substitution (eas) reactions between geraniol and 1,4-hydroquinone or p-methoxyphenol respectively, using bf3？et2o as a catalyst. furthermore, natural geranylquinone 3, geranyl-1,4-dimethoxyquinone 4 and the new geranyl-4-methoxyphenyl acetate 5 were obtained by chemical transformations of 1 and 2. the compounds were evaluated for their in vitro cytotoxicity activities against cultured human cancer cells of pc-3 human prostate cancer, mcf-7 and mda-mb-231 breast carcinoma, and dermal human fibroblasts dhf. ic50 values were in the μm range.