Synthesis and inhibitory activity of bromoquinone derivatives

Article abstract of DOI:10.1016/S0040-4020(01)85459-4

2,5 Dibromo-3-methyl-6-isopropyl-1,4-benzoquinone has been reported inhibitory to b6-f and b-c1 complexes [Malkin, R. (1977) Biochim. Biophys. Acta., 501, 552-554]. In this paper, four classes of the analogues are synthesized. They were 5-bromo-3-methyl, 3-bromo-2-methoxy-5-methyl, 2,5-dibromo-3-methyl, and 3,5-dibromo-2-methyl derivatives with the side chain -(CH₂)_nH of N=5,7,9,11 and 13 at position 6. Dibromo compounds are usually more inhibitory in the mitochondrial ubiquinol cytochrome c reductase; the maximal inhibition was usually with 9 methylene in a functional group.