Synthesis of Quinones having Carboxy- and Hydroxy-Alkyl Side Chains, and Their Effects on Rat-Liver Lysosomal Membrane

Abstract

In order to study the structure activity relationship of metabolites of ubiquinone, α-tocopherol and phylloquinone (Ia, b, c, IIa, b, c), 3-carboxy-2-butenyl (IIIa, b, c), 6-hydroxy-3-methyl-2-hexenyl (IVa, b, c), 4-hydroxy-3-methylbutyl (Va, b), 4-hydroxy-3-methyl-2-butenyl (VIb, c), ω-carboxyalkyl (VIIa, b, c), and ω-hydroxyalkyl (VIIIa, b) 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 (VIIa, b). © 1982, The Pharmaceutical Society of Japan. All rights reserved.