Abstract

Arylmethylenebis(3-hydroxy-5,5-dimethyl-2-cyclohexen-1-one) derivatives (aryl=2-hydroxynaphthyl (1) and 3,4-dihydroxyphenyl (2) have been synthesized and their structures have been elucidated. Both compounds were examined for their antioxidant, antimicrobial and cytotoxic activity. Antioxidative activities of synthesized compounds were evaluated by 2,2-diphenyl-1-picryl-hydrazyl (DPPH) and ferric reducing antioxidant power (FRAP) methods. The microbial screening was performed by diffusion method on bacterial strains Staphylococcus aureus, Enterococcus faecalis, Bacillus subtilis and Candida albicans. Cytotoxic activity was tested on liver hepatocellular carcinoma cell line (Hep G2) by Neutral red assay. Compared to compound 2, compound 1 showed better antimicrobial and antifungal activity, while compound 2 showed better antioxidant activity with IC50 of 0.0156 mM and FRAP value 50469.44 µmol/l Fe2+. Both compounds showed cytotoxic activity. Obtained results implicate the importance of arylmethylenebis(3-hydroxy-5,5-dimethyl-2-cyclohexen-1-on) derivatives as a potential antioxidant, antimicrobial and cytotoxic agents.

Key words: Tetraketones; cyclohexen-1-one derivatives; synthesis; antioxidants; antimicrobial screening; cytotoxic activity.