Effects of 4,4-dimethyl-5,8-dihydroxynaphtalene-1-one and 4,4-dimethyl-5,8-dihydroxytetralone derivatives on tumor cell respiration

Bioorg Med Chem. 2002 Sep;10(9):3057-60. doi: 10.1016/s0968-0896(02)00154-2.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Respiration / drug effects*
  • Drug Resistance, Multiple
  • Ketones / chemical synthesis
  • Ketones / pharmacology
  • Mice
  • Oxygen Consumption / drug effects
  • Phenols / chemical synthesis*
  • Phenols / pharmacology
  • Structure-Activity Relationship
  • Tumor Cells, Cultured

Substances

  • Ketones
  • Phenols