Hydrophobic Properties of Anticonvulsant Phenylacetanilides. Relationship between Octanol-Water Partition Coefficient and Capacity Factor Determined by Reversed-Phase Liquid Chromatography

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Partition coefficients (octanol-water), P. for a series of phenylacetanilides, PhCH_2CONHC_6H_4-X_<m, p> (I), were determined by the shaking-flask method. The observed π values (π=log P_<(I)>-log ρ_<phCH_2CONHPh>) were analyzed in terms of substituent effects to give the relationship π=0.833π_x+0.788σ_x+0.040,where π_x=log_<phx>-log_<phH>. We also determined and analyzed the capacity factors for these compounds, K', which are regarded as an alternative hydrophobic parameter, by using reversed-phase high-performance liquid chromatography (RP-HPLC) in different H_2O-organic solvent mixtures. It was observed that the substituent effects on the log κ' value are influenced by the organic modifier in the mobile phase. Linear relationships between log P and log κ' were generally observed but there were some outliers such as OH, CN and NO_2 derivatives. The deviation of phenolic compounds from the log ρ-log κ' linearity can be explained in terms of the difference in partitioning behavior between the octanol-water system and the lipophilic stationary phase-mobile phase system.
公益社団法人日本薬学会の論文
1984-12-25