Synthesis of quinones having carboxy- and hydroxy-alkyl side chains, and their effects on rat-liver lysosomal membrane.

Abstract
To study the structure-activity relationship of metabolites of ubiquinone, .alpha.-tocopherol and phylloquinone, 3-carboxy-2-butenyl, 6-hydroxy-3-methyl-2-hexenyl, 4-hydroxy-3-methylbutyl, 4-hydroxy-3-methyl-2-butenyl, .omega.-carboxyalkyl and .omega.-hydroxyalkyl side chains were introduced into the 6-position of 2,3-dimethoxy-5-methyl-1,4-benzoquinone and 2,3,5-trimethyl-1,4-benzoquinone as well as the 3-position of 2-methyl-1,4-naphthoquinone. The effects of these quinones on the membrane stability of rat-liver lysosomes and on the activity of bovine heart phosphodiesterase were investigated. A good correlation was observed between these activities of the benzoquinone derivatives.