Abstract
A series of the new urea derivatives with antinociceptive activity has been chromatographically evaluated using reversed phase materials: Zorbax Extend-C18, Cogent UDC Cholesterol with organic-aqueous eluent systems with two organic modifiers (methanol and acetonitrile). The chromatographic lipophilicity parameters: log kw, S and φ0 were determined basing on linear relationship between log k values and concentration of organic mobile phase modifier. The structure-retention studies revealed that the retention mechanism for all studied urea derivatives is uniform for the proposed chromatographic systems. However, a few exceptions were noticed. Derivatives containing nonpolar substituents in the imidazole ring acted as outliers for cholesterol column. In turn, the derivative containing ester polar substituent acted as an outlier in conventional reversed-phase system. Quantitative relationships based on a wide set of established computational molecular descriptors and experimental chromatographic data were also developed. Through a systematic study, by using the principal component analysis, fragmental method KowWIN appeared to be the most powerful software to produce reliable estimations of experimental retention parameters obtained on cholesterol column.
Highlights
Lipophilicity is one of the most important parameters in drug design, playing a key role in kinetic and dynamic aspects of drug action.[1]
Many of the current papers describe application of retention factors estimated by polycratic methods. According to this last approach, the chromatographic lipophilicity values are derived from the linear relationship between retention and the volume fraction (j) of organic solvent in the mobile phase.[13,14,15,16]
That peak symmetry was better for methanol containing eluent system on octadecyl silica stationary phase and for acetonitrile/water mobile phase on UDC Cholesterol column
Summary
Lipophilicity is one of the most important parameters in drug design, playing a key role in kinetic and dynamic aspects of drug action.[1] The importance of lipophilicity in predicting ADMET (absorption, distribution, metabolism, excretion, toxicity) properties has been well documented.[1,2,3]. It should be emphasized, that the number of existing experimental lipophilicity scales is extremely low in comparison to high number of compounds for which such data are essential.
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