Effects of 4,4-Dimethyl-5,8-dihydroxynaphtalene-1-one and 4,4-Dimethyl-5,8-dihydroxytetralone Derivatives onTumor Cell Respiration

Abstract

Abstract—A set of structurally related compounds incorporating a carbonyl group in the ortho position withregard to a phenol function were tested against the TA3 mouse carcinoma cell line and its multidrug-resistant variant TA3-MTX-R. The series consists of 20-hydroxyacetophenone, 40-hydroxyacetophenone 20,50-dihydroxyacetophenone, 4-acetyl-3,3-dimethyl-5-hydroxy-2-morpholino- 2,3-dihydrobenzobfuran, five 4,4-dimethyl-5,8-dioxygenated naphtalene-1-ones and three 4,4-dimethyl-5,8-dioxygenated tetralones. A tentative structure–activity relationship was found for this family of substances, suggesting that a coplanar ortho-carbonyl- 1,4-hydroquinone motif is able to cause inhibition of cellular respiration.