Synthesis and collagenase inhibition of new glycosides of aranciamycinone: the aglycon of the naturally occurring antibiotic aranciamycin.
Glycosides of aranciamycinone were prepared by glycosylation with sugar acetates and trimethylsilyl triflate in dichloromethane. Glycosides of the following sugars were prepared: alpha-L-rhamnopyranose, beta-D-glucopyranose, beta-D-ribopyranose, beta-D-xylopyranose, alpha-L-fucopyranose, 2-azido-2,6-dideoxy-alpha-L-mannopyranose, 2,6-dideoxy-alpha-L-arabino-hexopyranose, 3,6-dideoxy-alpha-L-arabino-hexopyranose, and 4,6-dideoxy-alpha-L-lyxo-hexopyranose. The new glycosides were tested for inhibition of Clostridium histolyticum collagenase and Yoshida Sarcoma tumor cells.
Bols
M
M
Department of Organic Chemistry, Technical University of Denmark, Lyngby.
Binderup
L
L
Hansen
J
J
Rasmussen
P
P
D000818:Animals; D018943:Anthracyclines; D000903:Antibiotics, Antineoplastic; D001551:Benz(a)Anthracenes; D004261:DNA Replication / Q000187:drug effects; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D003012:Microbial Collagenase / Q000037:antagonists & inhibitors*; D009279:Naphthacenes; D009904:Optical Rotation; D012517:Sarcoma, Yoshida; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
D018943:Anthracyclines; D000903:Antibiotics, Antineoplastic; D001551:Benz(a)Anthracenes; D006027:Glycosides; D007202:Indicators and Reagents; D009279:Naphthacenes; C075925:aranciamycin; C078961:aranciamycinone; D003012:Microbial Collagenase