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.
Johnsson
Richard
R
Organic Chemistry, Lund University, PO Box 124, SE-221 00 Lund, Sweden.
Mani
Katrin
K
Ellervik
Ulf
U
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D002240:Carbohydrate Sequence; D002460:Cell Line; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D002851:Chromatography, High Pressure Liquid; D003470:Culture Media; D006025:Glycosaminoglycans / Q000138:chemical synthesis* / Q000494:pharmacology*; D006031:Glycosylation; D006801:Humans; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008969:Molecular Sequence Data; D009281:Naphthalenes / Q000737:chemistry; D011134:Polysaccharides / Q000138:chemical synthesis / Q000494:pharmacology; D013329:Structure-Activity Relationship; D014994:Xylose / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology*
D000970:Antineoplastic Agents; D003470:Culture Media; D006025:Glycosaminoglycans; D007202:Indicators and Reagents; D009281:Naphthalenes; D011134:Polysaccharides; D014994:Xylose