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Synthesis of 5‐Alkynyl Isoxazolidinyl Nucleosides
Author(s) -
Romeo Roberto,
Giofrè Salvatore Vincenzo,
Iaria Daniela,
Sciortino Maria Teresa,
Ronsisvalle Simone,
Chiacchio Maria Assunta,
Scala Angela
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100767
Subject(s) - chemistry , sonogashira coupling , acetylene , cycloaddition , nucleoside , stereochemistry , palladium , alkyne , combinatorial chemistry , medicinal chemistry , catalysis , organic chemistry
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.