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Preparation and Hydro-lipophilic properties of monosubstituted N-aryl-4-hydroxyquinoline-3-carboxanilides
1 , 2 , 2 , 3 , 4 , * 2, 5
1  Department of Chemical Drugs, Faculty of Pharmacy, Masaryk University, Palackeho 1, 602 00 Brno, Czech Republic
2  Department of Analytical Chemistry, Faculty of Natural Sciences, Comenius University, Ilkovicova 6, 84215 Bratislava, Slovakia
3  Department of Chemical Drugs, Faculty of Pharmacy, Masaryk University, Palackeho 1946/1, 612 00 Brno, Czech Republic
4  Global Change Research Institute CAS, Belidla 986/4a, 603 00 Brno, Czech Republic
5  Institute of Neuroimmunology, Slovak Academy of Sciences, Dubravska Cesta 9, 845 10 Bratislava, Slovakia
Academic Editor: Julio A. Seijas


A series of twenty-two monosubstituted N-aryl-4-hydroxyquinoline-3-carboxanilides designed as dual anti-invasive agents was prepared and characterized. Lipophilicity significantly affects biological activities of compounds and ADME properties, therefore the lipo-hydrophilic properties of these 4-hydroxyquinoline-3-carboxanilides were investigated. All the derivatives were analyzed by reversed-phase high-performance liquid chromatography. The procedure was carried out under isocratic conditions with methanol as the organic modifier in the mobile phase using an end-capped non-polar C18 stationary reversed-phase column. In this study, correlations between the logarithm of the capacity factor k and log P/Clog P values calculated by various methods are discussed, as well as the relationships between lipophilicity and chemical structure of the studied compounds.

Keywords: hydroxyquinoline-carboxanilides; synthesis; lipiphilicity