Abstract

New 1′,2′- cis-disubstituted 8-azapurine-based carbocyclic analogues of nucleosides with or without a methylene between the carbocycle and the base were synthesised, starting from appropriate amino alcohols, via 6-chloro-8-azapurines; their antiviral and antitumoral activities were evaluated; and their structures were compared with that of 2′,3′-dideoxyadenosine (ddA) on the basis of AM1 calculations. No new compound had antiviral activity. The one with the best overall antitumoral activity against L1210, Molt4/C8 and CEM/0 cells, compound 10, was that in which the position of the hydroxymethyl group on the carbocycle relative to the heterocyclic base was closest to that found in the best-fitting low-energy conformer of ddA.

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