Synthesis and Antiviral Evaluation of (-)-3′-Methylcarbovir, (-)-3′-Methylabacavir, and Modified Purine Analogues

Abstract

Starting from ethyl (1S,4R)-4-hydroxy-2-methylcyclopent-2-ene-1-carboxylate, as a common enantiopure building block readily obtained by enzymatic kinetic resolution of the corresponding racemic derivative, 3′-methylcarbovir, 3′-methylabacavir, and three modified analogues were synthesized via the linear construction of the purine heterocycles. These derivatives were evaluated as potential agents against HIV-1, HIV-2, and other important viral pathogens. None of the new compounds had significant antiviral activity at a concentration of 100 µg˙mL^-¹, which was the highest concentration tested.

Key words

stereoselective synthesis - azides - carbocyclic nucleosides - nucleobases - antiviral agents

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