Synthesis and biological activity of some unsaturated 6-azauracil acyclonucleosides.
A useful route is described for obtaining Z and E unsaturated alkylating agents 3 and 4. Coupling 6-azauracils 5 and 6 with unsaturated alkylating agent followed by the deprotection with H+ resin gave acyclonucleosides 11-14 in good overall yields. Unsaturated acyclonucleosides phosphonates 19 and 20 were prepared using potassium carbonate as base and 4-bromobut-2-enyl diethyl phosphonate 16 as the alkylating agent. The introduction of a propargyl group at the N-3 position of acyclonucleosides 7, 8 17, 18, 19, and 20 was achieved using potassium carbonate in DMF.
Kabbaj
Youssef
Y
Laboratory of Bio-Organic Chemistry, Faculty of Sciences Semlalia, Marrakesh, Morocco.
Lazrek
Hassan Bihi
HB
Barascut
Jean Louis
JL
Imbach
Jean Louis
JL
D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D015497:HIV-1 / Q000187:drug effects; D015498:HIV-2 / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D014498:Uracil / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
D000998:Antiviral Agents; D014498:Uracil; C100248:azauracil