4'- and 1'-methyl-substituted 5'-norcarbanucleosides.
5'-norcarbocyclic nucleosides have been found to possess a variety of meaningful biological properties. Derivatives of these compounds possessing substituents at the hydroxyl and heterocyclic ring bearing carbon atoms have not been described. As entries into these compounds, the 4'- and 1'-methyl derivatives of 5'-noraristeromycin (2 and 3) have been prepared from a common cyclopentyl precursor 8. The synthetic methods developed are adaptable to 5'-norcarbanucleosides possessing a variety of heterocyclic bases and in the l-like configuration. In turn, the products from such syntheses will lend themselves to a number of structural and biochemical investigations relevant to carbanucleosides in general. Compounds 2 and 3 lack antiviral properties and were not cytotoxic.
Roy
Atanu
A
Department of Chemistry, Auburn University, Auburn, Alabama 36849-5312, USA.
Schneller
Stewart W
SW
D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000998:Antiviral Agents; D009705:Nucleosides; C076829:5'-noraristeromycin; D000241:Adenosine