Novel carbocyclic nucleosides containing a cyclobutyl ring. Guanosine and adenosine analogues.
(1R,cis)-2-(3-Amino-2,2-dimethylcyclobutyl)ethanol (4) was used as a precursor in the synthesis of cyclobutyl nucleoside analogues containing guanine, 8-azaguanine, adenine or 8-azaadenine. All the compounds were evaluated as antiviral agents in a variety of assay systems. Some activity was noted for compound 13, 17, 19 and 20 against vaccinia virus and for compounds 11, 12, 13, 17, 19 and 20 against herpes simplex virus, at concentrations that were up to 10-fold below the cytotoxic concentrations for the host cells.
Departamento de Química Orgánica, Facultade de Farmacia, Universidade de Santiago, Spain.
J E
JE
Borges
F
F
Fernández
X
X
García
A R
AR
Hergueta
C
C
López
G
G
Andrei
R
R
Snoeck
M
M
Witvrounw
J
J
Balzarini
E
E
De Clercq
D000146:Acids, Carbocyclic; D000241:Adenosine / Q000031:analogs & derivatives* / Q000737:chemistry; D000998:Antiviral Agents / Q000138:chemical synthesis*; D006151:Guanosine / Q000031:analogs & derivatives*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D009705:Nucleosides / Q000737:chemistry*
D000146:Acids, Carbocyclic; D000998:Antiviral Agents; D009705:Nucleosides; D006151:Guanosine; C030034:aristeromycin; D000241:Adenosine