Synthesis of biologically active polyphenolic glycosides (combretastatin and resveratrol series).
(E)-3-(beta-D-Glucopyranosyloxy)-4',5-dihydroxystilbene (resveratrol 3-beta-D-glucoside, piceid), (Z)-2',3'-dihydroxy-3,4,4',5-tetramethoxystilbene (combretastatin A-1), (Z)-3'-hydroxy-3,4,4',5-tetramethoxystilbene (combretastatin A-4), (Z)-2'-hydroxy-3-4-4'-5-tetramethoxystilbene (combretastatin iso-A-4), alpha, beta-dihydro-2',3'-dihydro-2',3'-dihydroxy-3,4,4',5-tetramethoxystilb ene (combretastatin B-1), the corresponding glucosides, and related compounds have been synthesized via Wittig reactions followed by glucosylation under phase-transfer catalysis. Most of the compounds synthesized have been tested with respect to biological activity (cytostatic, cytotoxic, antimitotic, neurotoxic, antiplatelet, aggregation activity).
Orsini
F
F
Centro di Studio per le Sostanze Organiche Naturali del CNR, Dipartimento di Chimica Organica e Industriale, Milano, Italy.
Pelizzoni
F
F
Bellini
B
B
Miglierini
G
G
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000494:pharmacology; D001632:Bibenzyls / Q000138:chemical synthesis* / Q000494:pharmacology; D002455:Cell Division / Q000187:drug effects; D005727:Ganglia, Spinal / Q000187:drug effects / Q000502:physiology; D005960:Glucosides / Q000138:chemical synthesis* / Q000494:pharmacology; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008938:Mitosis / Q000187:drug effects; D015394:Molecular Structure; D010975:Platelet Aggregation Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D000077185:Resveratrol; D013267:Stilbenes / Q000138:chemical synthesis* / Q000494:pharmacology; D014407:Tumor Cells, Cultured
D000970:Antineoplastic Agents; D001632:Bibenzyls; D005960:Glucosides; D010975:Platelet Aggregation Inhibitors; D013267:Stilbenes; C040105:combretastatin; D000077185:Resveratrol