Chemoenzymatic synthesis and antiviral evaluation of conformationally constrained and 3'-methyl-branched carbanucleosides using both enantiomers of the same building block.
Starting from both enantiomers of a readily available building block, a straightforward enantioselective approach to constrained 3'-methyl-2',3'-alpha-oxirane-fused and 3'-methyl-3',4'-alpha-oxirane-fused carbanucleosides bearing different purine base analogues is described. The title compounds were evaluated as potential antiviral agents against important viruses. None of the new compounds had significant antiviral activity at a concentration of 100 microg/mL, which was the highest concentration tested.
Aubin
Yoann
Y
Laboratoire de Réactivité Organique Sélective, U.M.R. 6180 Chirotechnologies: catalyse et biocatalyse, Université Paul Cézanne, Aix-Marseille III, 13397 Marseille Cedex 20, France.
Audran
Gérard
G
Monti
Honoré
H
De Clercq
Erik
E
D000998:Antiviral Agents / Q000737:chemistry* / Q000494:pharmacology; D005027:Ethylene Oxide / Q000737:chemistry; D009690:Nucleic Acid Conformation; D009705:Nucleosides / Q000737:chemistry* / Q000494:pharmacology; D011684:Purine Nucleosides / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000998:Antiviral Agents; D009705:Nucleosides; D011684:Purine Nucleosides; D005027:Ethylene Oxide