Partial synthesis and antitubulin activity of minor colchicum alkaloids: N-acetoacetyl-deacetylcolchicine and 2-demethylspeciosine (speciocolchine).
Two minor Colchicum alkaloids, N-acetoacetyl-deacetylcolchicine [1] and 2-demethylspeciosine [7], were synthesized. The diacetate 8 of 2-demethylspeciosine was also prepared. The antitubulin activity of these compounds, in comparison to colchicine, was measured. N-Acetoacetyl-deacetylcolchicine [1] has in vitro activity similar to that of colchicine. Both 2-demethylspeciosine [7] and the diacetate 8 were considerably less potent inhibitors of tubulin polymerization.
Muzaffar
A
A
Section on Natural Products, Laboratory of Structural Biology, NIDDK, Bethesda, Maryland 20892.
Brossi
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A
Hamel
E
E
D000470:Alkaloids / Q000138:chemical synthesis* / Q000494:pharmacology; D003078:Colchicine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D003079:Colchicum; D015394:Molecular Structure; D010946:Plants, Medicinal; D011108:Polymers; D014404:Tubulin / Q000096:biosynthesis / Q000187:drug effects*
D000470:Alkaloids; D011108:Polymers; D014404:Tubulin; C069176:2-demethylspeciosine; C069178:N-acetoacetyl-N-deacetylcolchicine; D003078:Colchicine