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Rhodanineacetic Acid Derivatives as Potential Drugs: Preparation and Hydrophobic Properties of 5-Arylalkylidene-3-carboxymethylrhodanines
1 , * 2, 3 , 1 , 1 , 1, 3
1  Department of Pharmaceutical Chemistry and Drug Control, Charles University in Prague, Faculty of Pharmacy in Hradec Kralove, 500 05 Hradec Kralove, Czech Republic
2  Zentiva a.s., U kabelovny 130, 102 37 Prague 10, Czech Republic
3  Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 61242 Brno, Czech Republic

Abstract: Some (5-arylalkylidene-4-oxo-2-thioxothiazolidin-3-yl)acetic acids were prepared as potential antimicrobial compounds. General synthetic approach of all synthesized compounds is presented. All the discussed rhodanine-3-acetic acid derivatives were analyzed using the reversed phase high performance liquid chromatography (RP-HPLC) method for the lipophilicity measurement. The procedure was performed under isocratic conditions with methanol as an organic modifier in the mobile phase using end-capped non-polar C18 stationary RP column. RP-HPLC retention parameter log k (the logarithm of capacity factor k) is compared with log P values calculated in silico. The relationships between the lipophilicity and chemical structure of the studied compounds are discussed as well.
Keywords: 5-Arylalkylidenerhodanine-3-acetic acid derivatives; Lipophilicity measurement; Structure-lipophilicity relationships