Lipophilicity of 5 '-carbonates of lamivudine with antiretroviral activity. Correlation between different methods

This study reports on the lipophilicity of novel 5'-carbonates of lamivudine with anti-HIV activity. Reversed-phase thin layer chromatography (RP-TLC), reversed-phase high performance liquid chromatography (RP-HPLC), conventional shake flask (log P-oct), and the theoretical CLOGP methods were used, in order to establish if the linear relationships between the conventional and chromatographic methods permit an extrapolation procedure. The nature of the organic modifiers used in the chromatographic techniques did not substantially affect the measurement of lipophilicity, since a good correlation between experimental log P-oct and extrapolated RP-TLC and RP-HPLC values (R-Mw and log k'(w), respectively) supported the validity of the extrapolation technique.