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Preparation and Hydro-lipophilic Properties of Novel Fluorinated Benzyl Carbamates of 4-Aminosalicylanilides
1, 2 , 1 , 3 , 1 , * 1, 4
1  Department of Analytical Chemistry, Faculty of Natural Sciences, Comenius University, Ilkovicova 6, 84215 Bratislava, Slovakia
2  NT-LAB o.z., Teplicka 35, 921 01 Piestany, Slovakia
3  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
4  Institute of Neuroimmunology, Slovak Academy of Sciences, Dubravska Cesta 9, 845 10 Bratislava, Slovakia


A series of seven fluorinated benzyl carbamates of 4-aminosalicylanilides and unsubstituted benzyl [3-hydroxy-4-(phenylcarbamoyl)phenyl]carbamate designed as agents with the expected anticholinesterase and anti-inflammatory activity were prepared and characterized. As lipophilicity significantly influences the biological activity of compounds, the hydro-lipophilic properties of these mono-, di- and tri-substituted carbamates were investigated in the study. All the discussed derivatives 4-{[(benzyloxy)carbonyl]amino}-2-hydroxybenzoic acid 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, logarithm of the distributive parameter D at pH 7.4 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: 4-Aminosalicylanilides; Carbamates; Synthesis; Lipophilicity determinations; Structure-lipophilicity relationships