New pseudonucleosides containing chiral oxazolidin-2-ones and cyclosulfamides as aglycones: synthesis and antiviral evaluation.
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 beta-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.
Bouleghlem
Hocine
H
Laboratoire de Chimie Organique Appliquée (LCOA), Groupe de Chimie Bioorganique, Faculté des Sciences. Université d'Annaba, Annaba, Algéria.
Berredjem
Malika
M
Lecouvey
Marc
M
Aouf
Nour-Eddine
NE
D000596:Amino Acids / Q000737:chemistry*; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D018259:Herpesvirus 1, Human / Q000187:drug effects; D018258:Herpesvirus 2, Human / Q000187:drug effects; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D023303:Oxazolidinones / Q000737:chemistry*; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry*; D014616:Vaccinia virus / Q000187:drug effects
D000596:Amino Acids; D000998:Antiviral Agents; D006571:Heterocyclic Compounds; D009705:Nucleosides; D023303:Oxazolidinones; D013449:Sulfonamides