Starting with 5-iodo N,O-nucleosides, prepared by 1,3-dipolar cycloaddition of nitrones with vinyliodouracil, or vinyl acetate followed by coupling with silylated iodouracil, a series of 5-alkynyl N,O-nucleosides were synthesized via a palladium-catalyzed (Sonogashira) coupling reaction. The cytotoxic activity of modified nucleosides against HEp-2 cell lines was determined in vitro. The 5-ethynyl N,O-nucleoside, the only compound in the series containing a terminal acetylene unit, was found to be the most active compound.
Synthesis of 5-Alkynyl Isoxazolidinyl Nucleosides
ROMEO, Roberto;GIOFRE', Salvatore Vincenzo;SCIORTINO, Maria Teresa;SCALA, ANGELA
2011
Abstract
Starting with 5-iodo N,O-nucleosides, prepared by 1,3-dipolar cycloaddition of nitrones with vinyliodouracil, or vinyl acetate followed by coupling with silylated iodouracil, a series of 5-alkynyl N,O-nucleosides were synthesized via a palladium-catalyzed (Sonogashira) coupling reaction. The cytotoxic activity of modified nucleosides against HEp-2 cell lines was determined in vitro. The 5-ethynyl N,O-nucleoside, the only compound in the series containing a terminal acetylene unit, was found to be the most active compound.File in questo prodotto:
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