Next Article in Journal
Chemical Composition and in Vitro Antimicrobial and Mutagenic Activities of Seven Lamiaceae Essential Oils
Next Article in Special Issue
Synthesis, Antimycobacterial, Antifungal and Photosynthesis-Inhibiting Activity of Chlorinated N-phenylpyrazine-2-carboxamides
Previous Article in Journal
New Flavonoid Glycosides from Elsholtzia rugulosa Hemsl.
Previous Article in Special Issue
Examination of Imprinting Process with Molsidomine as a Template
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,*
Received: 21 September 2009; in revised form: 9 October 2009 / Accepted: 19 October 2009 / Published: 20 October 2009
(This article belongs to the Special Issue ECSOC-12)
Download PDF [270 KB, uploaded 18 June 2014]
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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Export to BibTeX |
EndNote


MDPI and ACS Style

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.

AMA Style

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(10):4197-4212.

Chicago/Turabian Style

Dolezel, Jan; Hirsova, Petra; Opletalova, Veronika; Dohnal, Jiri; Marcela, Vejsova; Kunes, Jiri; Jampilek, Josef. 2009. "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 14, no. 10: 4197-4212.


Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert