Novel carbocyclic nucleosides containing a cyclobutyl ring: adenosine analogues.
(1S,1'R)-cis-1-(3'-aminomethyl-2',2'-dimethylcyclobutyl)ethanol (1) and (1S,1'R)-cis-1-[3'-(2-aminoethyl)-2',2'-dimethylcyclobutyl]ethanol (2) were used as precursors in the synthesis of cyclobutyl nucleoside analogues containing adenine and 8-azaadenine moieties, which were tested as antiviral and antitumoral agents in a variety of assay systems. Compounds 8 and 9 displayed significant activity against respiratory syncytial virus, and compounds 14 and 15 were moderately active against vaccinia virus.
Hergueta
A R
AR
Departmento de Química Orgánica, Facultad de Farmacia, Universidad de Santiago, Santiago de Compostela, Spain.
Fernandez
F
F
López
C
C
Balzarini
J
J
De Clercq
E
E
D000241:Adenosine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D003503:Cyclobutanes / Q000737:chemistry*; D000431:Ethanol / Q000031:analogs & derivatives / Q000737:chemistry*; D006367:HeLa Cells; D006801:Humans; D007202:Indicators and Reagents; D009705:Nucleosides / Q000737:chemistry* / Q000494:pharmacology; D018113:Respiratory Syncytial Virus, Human / Q000187:drug effects; D014407:Tumor Cells, Cultured; D014616:Vaccinia virus / Q000187:drug effects
C446964:1-(3'-aminomethyl-2',2'-dimethylcyclobutyl)ethanol; D000970:Antineoplastic Agents; D000998:Antiviral Agents; D003503:Cyclobutanes; D007202:Indicators and Reagents; D009705:Nucleosides; D000431:Ethanol; D000241:Adenosine