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. 2009 Oct 20;14(10):4197-212.
doi: 10.3390/molecules14104197.

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  1 , Petra Hirsova, Veronika Opletalova, Jiri Dohnal, Vejsova Marcela, Jiri Kunes, Josef Jampilek
Affiliations

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 et al. Molecules. .

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 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.

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Figures

Figure 1
Figure 1
Structure of epalrestat.
Scheme 1
Scheme 1
Synthesis and structures of the target 5-substituted rhodanine-3-acetic acid derivatives 1-9.
Figure 2
Figure 2
Comparison of the log P data calculated using the two programs with the experimentally found log k values. The compounds are arranged in the ascending manner according to the experimental log k values.
Figure 3
Figure 3
Structure of compound 10, PMT1 inhibitor.
See this image and copyright information in PMC

References

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