Synthesis and biological evaluation of diastereoisomerically pure N,O-nucleosides

Several N,O-nucleosides have been synthesized in good yields by direct 1,3-dipolar cyclization methodology, in the absence of solvent. A remarkable cis stereoselectivity (de 98%) was observed by tuning the substituents on the nitrone moiety. A good number of these N,O-nucleosides have been evaluated for cytotoxic activity against selected cellular lines. Some of the tested compounds have proven to be potential antiproliferative drugs.

The synthesis of some new N,O-nucleosides is described, based on the 1,3-dipolar cycloaddition of nitrones and unprotected vinyl nucleobases. Promising results were found during their biological evaluation.Figure optionsDownload as PowerPoint slide