Synthesis, antiviral and cytostatic activities of carbocyclic nucleosides incorporating a modified cyclopentane ring. Part 2: Adenosine and uridine analogues.
Six new carbocyclic nucleosides were prepared by mounting a purine (compounds 5-7), 8-azapurine (compounds 9 and 10) or pyrimidine (compound 13) base on the amino group of (1R,cis)-3-(aminomethyl)-1,2,2-trimethylcyclopentylmethanol (2). The antiviral activity of compounds 5-7, 10 and 13, and their cytostatic activity, were evaluated. At subtoxic concentrations, the compounds showed no or marginal antiviral activity. Compound 5 showed moderate inhibition on tumor cell proliferation.
Departamento de Química Orgánica, Facultade de Farmacia, Universidade de Santiago, Spain.
M I
MI
Nieto
J M
JM
Blanco
O
O
Caamaño
F
F
Fernández
X
X
García-Mera
J
J
Balzarini
E
E
Padalko
J
J
Neyts
E
E
De Clercq
D000225:Adenine / Q000031:analogs & derivatives / Q000737:chemistry; D000241:Adenosine / Q000031:analogs & derivatives*; D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D002455:Cell Division / Q000187:drug effects; D003517:Cyclopentanes / Q000737:chemistry*; D008956:Models, Chemical; D014407:Tumor Cells, Cultured; D014498:Uracil / Q000031:analogs & derivatives; D014529:Uridine / Q000031:analogs & derivatives*
D000998:Antiviral Agents; D003517:Cyclopentanes; D014498:Uracil; D000225:Adenine; D000241:Adenosine; D014529:Uridine; C006654:8-azaadenine