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Preparation and Hydro-lipophilic Properties of Methoxylated and Methylated 1-Hydroxynaphthalene-2-Carboxanilides
Josef Jampilek * 1, 2 , Iva Kapustikova 3 , Tomas Gonec 4 , Jiri Kos 3 , Ewelina Spaczynska 5 , Michal Oravec 6 , Jana Dohanosova 7 , Tibor Liptaj 7 , Robert Musiol 5
1  Department of Analytical Chemistry, Faculty of Natural Sciences, Comenius University, Ilkovicova 6, 84215 Bratislava, Slovakia
2  Division of Biologically Active Complexes and Molecular Magnets, Regional Centre of Advanced Technologies and Materials, Faculty of Science, Palacky University, Slechtitelu 27, 78371 Olomouc, Czech Republic
3  Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Comenius University, Odbojarov 10, 832 32 Bratislava, Slovakia
4  Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1, 612 42 Brno, Czech Republic
5  Institute of Chemistry, University of Silesia, 75 Pulku Piechoty 1a, 41 500 Chorzow, Poland
6  Global Change Research Institute CAS, Belidla 986/4a, 603 00 Brno, Czech Republic
7  Central Laboratories, Faculty of Chemical and Food Technology, Slovak University of Technology in Bratislava, Radlinskeho 9, Bratislava 812 37, Slovakia


A series of variously methoxylated and methylated N-aryl-1-hydroxynaphthalene-2-carboxanilides was prepared and characterized as potential anti-invasive agents. As it is known that lipophilicity significantly influences the biological activity of compounds, the hydro-lipophilic properties of these mono-, di- and tri-substituted 1-hydroxynaphthalene-2-carboxanilides are investigated in the study. All the discussed hydroxynaphthalene derivatives were analysed using the reversed-phase high performance liquid chromatography method to measure lipophilicity. 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 correlations between the logarithm of the capacity factor k and log P/Clog P values calculated in various ways as well as the relationships between the lipophilicity and the chemical structure of the studied compounds are discussed.

Keywords: Hydroxynaphthalenecarboxamides; Synthesis; Lipophilicity determinations; Structure-lipophilicity relationships