New Pseudonucleosides Containing Chiral Oxazolidin-2-Ones and Cyclosulfamides as Aglycones: Synthesis and Antiviral Evaluation

Abstract

A series of chiral cyclosulfamides and oxazolidinon-2-ones have been synthesized starting from aminoacids. Regioselective substitution of these pseudopyrimidic heterocyles was carried out under Mitsunobu conditions. Best substitution results were obtained by preliminary deprotection of cyclosulfamides and their condensation with β -D-ribofuranose. Chiral oxazolidin-2-ones were coupled directly with D-ribofuranose. All compounds were tested against HSV-2, VV and SV viruses. Two compounds 6b and 6e showed significant activities against HSV-type 1.

Keywords:

• Aminoacids
• cyclosulfamides
• oxazolidin-2-ones
• glycosylation
• pseudonucleosides
• Mitsunobu reaction

Dedicated to the loving memories of Pr. M. Abdessamad Guellati (1955–2006).

This work is partially supported by: Algerian Ministry of Scientific Research, CNEPRU Project No. E01120060035, Applied Organic Chemistry Laboratory (FNR 2000), and National Fund of Research. Fruitful discussions with Ms H. Mesbahi (Faculty of Science) are greatly appreciated.