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.
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 C(18) 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.
Dolezel
Jan
J
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. veronika.opletalova@faf.cuni.cz
Hirsova
Petra
P
Opletalova
Veronika
V
Dohnal
Jiri
J
Marcela
Vejsova
V
Kunes
Jiri
J
Jampilek
Josef
J
D000085:Acetates / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D041221:Candida glabrata / Q000187:drug effects; D041022:Candida tropicalis / Q000187:drug effects; D012236:Rhodanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D053778:Thiazolidines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D014250:Trichosporon / Q000187:drug effects
D000085:Acetates; D000935:Antifungal Agents; D053778:Thiazolidines; C038131:epalrestat; D012236:Rhodanine