EventsThe 12th International Electronic Conference on Synthetic Organic Chemistry
Published
This submission belongs to the session c. Bioorganic Chemistry and Natural Products of the event The 12th International Electronic Conference on Synthetic Organic Chemistry
Published date
25 Nov, 2008
Citation
Veronika Opletalova, Josef Jampilek, Jan Dolezel, Petra Hirsova, Jiri Dohnal, Rhodanineacetic Acid Derivatives as Potential Drugs: Preparation and Hydrophobic Properties of 5-Arylalkylidene-3-carboxymethylrhodanines, in Proceedings of The 12th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2008, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-12-01242
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Rhodanineacetic Acid Derivatives as Potential Drugs: Preparation and Hydrophobic Properties of 5-Arylalkylidene-3-carboxymethylrhodanines

Veronika Opletalova 1
Jan Dolezel 1
Petra Hirsova 1
Jiri Dohnal 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
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