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

Jan Dolezel, Petra Hirsova, Veronika Opletalova, Jiri Dohnal, Vejsova Marcela, Jiri Kunes, Josef Jampilek

Research output: Contribution to journalArticlepeer-review

38 Scopus citations

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/Iand Trichosporon asahii 1188.

Original languageEnglish (US)
Pages (from-to)4197-4212
Number of pages16
JournalMolecules
Volume14
Issue number10
DOIs
StatePublished - Oct 2009

Keywords

  • In vitro antifungal activity
  • Lipophilicity measurement
  • Synthesis
  • [(5Z)-(5-arylalkylidene-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)]acetic acids

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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