Synthesis and biology of bis-xylosylated dihydroxynaphthalenes.

The 10 analogous bis-xylosylated dihydroxynaphthalenes have been synthesized and their chemical and biological properties investigated. The yield of the xylosylation reactions can be correlated to the electrostatic potential, and thus to the nucleophilicity, for the oxygen atoms of the dihydroxynaphthalenes. The bis-xylosylated compounds were more stable compared to the mono-xylosylated ones. They initiate priming of glycosaminoglycan chains to less extent but the priming proceeds in two directions. Contrary to the mono-xylosylated analogs, the tested compounds did not show any antiproliferative properties.