Chromatographic and Computational Study of Hydro-lipophilic Properties of &lt;em&gt;N&lt;/em&gt;-Alkoxyphenylhydroxy-naphthalenecarboxamides

Josef Jampilek,Jiri Kos,Iva Kapustikova,Tomas Gonec

doi:10.3390/ecsoc-21-04719

Abstract

N-Alkoxy-3-hydroxynaphthalene-2-carboxanilides, N-alkoxy-1-hydroxynaphthalene-2-carboxanilides and N-alkoxy-2-hydroxynaphthalene-1-carboxanilides were recently reported as series of compounds with antimycobacterial, antibacterial and herbicidal activity. As it was found that the lipophilicity of these significantly biologically effective agents determined their activity, in this study hydro-lipophilic properties of all three series are investigated. All fifty-seven anilides were analysed using the reversed-phase high performance liquid chromatography method for lipophilicity measurement. The procedure was performed under isocratic conditions with methanol as an organic modifier in the mobile phase using an end-capped non-polar C18 stationary reversed-phase column. In the present study, the correlation between the logarithm of capacity factor k and log P/Clog P values calculated in various ways is discussed as well as the relationships between the lipophilicity and the chemical structure of the studied compounds.

Highlights

One of the major prerequisites for pharmacological screening and drug development is the prediction of absorption, e.g. the transport of a molecule through membranes
The drugs most frequently cross biological barriers by the passive transport, which strongly depends on the lipophilicity
A general procedure is the measurement of directly accessible retention time under isocratic conditions with varying amounts of an organic modifier in the mobile phase using end-capped non-polar C18 stationary RP columns and calculating the capacity factor k [4,5,6,7,8]

Summary

Introduction

One of the major prerequisites for pharmacological screening and drug development is the prediction of absorption, e.g. the transport of a molecule through membranes. A general procedure is the measurement of directly accessible retention time under isocratic conditions with varying amounts of an organic modifier in the mobile phase using end-capped non-polar C18 stationary RP columns and calculating the capacity factor k [4,5,6,7,8]. Since it was found that the lipophilicity of these significantly biologically effective agents determined their activity, in this study hydrolipophilic properties of all three series are investigated.

Results

Conclusion