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Molecules 2009, 14(10), 4197-4212; doi:10.3390/molecules14104197
Article

Rhodanineacetic Acid Derivatives as Potential Drugs: Preparation, Hydrophobic Properties and Antifungal Activity of (5-Arylalkylidene-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)acetic Acids

1
,
1
,
1
,
2,3
,
4
,
5
 and
2,3,*
1 Department of Pharmaceutical Chemistry and Drug Control, Faculty of Pharmacy in Hradec Kralove, Charles University in Prague, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic 2 Zentiva k.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, 612 42 Brno, Czech Republic 4 Department of Clinical Microbiology, Charles University Medical School and Teaching Hospital, Sokolska 581, Hradec Kralove 500 05, Czech Republic 5 Department of Inorganic and Organic Chemistry, Faculty of Pharmacy in Hradec Kralove, Charles University in Prague, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic
* Author to whom correspondence should be addressed.
Received: 21 September 2009 / Revised: 9 October 2009 / Accepted: 19 October 2009 / Published: 20 October 2009
(This article belongs to the Special Issue ECSOC-12)
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Abstract

Some [(5Z)-(5-arylalkylidene-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)]acetic acids were prepared as potential antifungal compounds. The general synthetic approach to all synthesized compounds is presented. Lipophilicity of all the discussed rhodanine-3-acetic acid derivatives was analyzed using a reversed phase high performance liquid chromatography (RP-HPLC) method. 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 RP column. The RP-HPLC retention parameter log k (the logarithm of the capacity factor k) is compared with log P values calculated in silico. All compounds were evaluated for antifungal effects against selected fungal species. Most compounds exhibited no interesting activity, and only {(5Z)-[4-oxo-5-(pyridin-2- ylmethylidene)-2-thioxo-1,3-thiazolidin-3-yl]}acetic acid strongly inhibited the growth of Candida tropicalis 156, Candida krusei E 28, Candida glabrata 20/I and Trichosporon asahii 1188.
Keywords: [(5Z)-(5-arylalkylidene-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)]acetic acids; synthesis; lipophilicity measurement; in vitro antifungal activity [(5Z)-(5-arylalkylidene-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)]acetic acids; synthesis; lipophilicity measurement; in vitro antifungal activity
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Dolezel, J.; Hirsova, P.; Opletalova, V.; Dohnal, J.; Marcela, V.; Kunes, J.; Jampilek, J. Rhodanineacetic Acid Derivatives as Potential Drugs: Preparation, Hydrophobic Properties and Antifungal Activity of (5-Arylalkylidene-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)acetic Acids. Molecules 2009, 14, 4197-4212.

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