Effects of 4,4-dimethyl-5,8-dihydroxynaphtalene-1-one and 4,4-dimethyl-5,8-dihydroxytetralone derivatives on tumor cell respiration.
A set of structurally related compounds incorporating a carbonyl group in the ortho position with regard 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 2'-hydroxyacetophenone, 4'-hydroxyacetophenone 2',5'-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.
Araya-Maturana
Ramiro
R
Department of Organic and Physical Chemistry, Faculty of Chemical and Pharmaceutical Sciences, University of Chile, Casilla 233, Santiago 1, Chile. raraya@ciq.uchile.cl
Delgado-Castro
Tomás
T
Gárate
Mario
M
Ferreira
Jorge
J
Pavani
Mario
M
Pessoa-Mahana
Hernán
H
Cassels
Bruce K
BK
D000818:Animals; D019069:Cell Respiration / Q000187:drug effects*; D018432:Drug Resistance, Multiple; D007659:Ketones / Q000138:chemical synthesis / Q000494:pharmacology; D051379:Mice; D010101:Oxygen Consumption / Q000187:drug effects; D010636:Phenols / Q000138:chemical synthesis* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
D007659:Ketones; D010636:Phenols