Carbocyclic 5'-noruridine.
A convenient preparation of (1'R,2'S,3'R,4'S)-1-(2',3',4'-trihydroxycyclopent-1'-yl)-1H-uracil (carbocyclic 5'-noruridine, 1) is described in 2 steps from the palladium complex of (+)-(1R,4S)-4-hydroxy-2-cyclopenten-1-yl acetate (3) and the sodium salt of uracil (2). Compound 1 was sought as a previously unknown member of the series of carbocyclic 5'-nor nucleosides needed as moieties for new oligomers. With 1 available, its antiviral properties and those of its enantiomer (5) are reported with 5 showing promising activity towards Epstein-Barr virus.
Hegde
V R
VR
Department of Chemistry, Auburn University, AL 36849-5312, USA.
Seley
K L
KL
Schneller
S W
SW
D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D004797:Enzyme-Linked Immunosorbent Assay; D006515:Hepatitis B virus / Q000187:drug effects; D004854:Herpesvirus 4, Human / Q000187:drug effects; D018139:Simplexvirus / Q000187:drug effects; D013237:Stereoisomerism; D014498:Uracil / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D014616:Vaccinia virus / Q000187:drug effects; D014721:Vesicular stomatitis Indiana virus / Q000187:drug effects
C411242:1-(2',3',4'-trihydroxycyclopent-1'-yl)-1H-uracil; D000998:Antiviral Agents; D014498:Uracil