Synthesis and anti-HIV activity of carbamates of antiviral agent stavudine

An efficient synthesis of carbamate analogues of the NRTI compound stavudine, has been achieved in five steps starting from commercially available thymidine. The synthesis involves conversion of thymidine into stavudine followed by condensation with carbaimidazole derivative obtained from various aromatic and heterocyclic amines in dimethylformamide solvent. The analogues thus obtained were further purified by crystallization to furnish analytically pure products. Examination of biological activity of these carbamate derivatives of stavudine showed that they inhibited HIV replication only at micro-molar concentrations.