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 revers...
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| Format: | Article |
| Language: | English |
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MDPI AG
2009-10-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/14/10/4197/ |
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| author | Josef Jampilek Jiri Kunes Vejsova Marcela Petra Hirsova Jiri Dohnal Veronika Opletalova Jan Dolezel |
| author_facet | Josef Jampilek Jiri Kunes Vejsova Marcela Petra Hirsova Jiri Dohnal Veronika Opletalova Jan Dolezel |
| author_sort | Josef Jampilek |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-04-13T05:04:13Z |
| format | Article |
| id | doaj.art-1be9977df27f45ce8a7cdf07aa5090dc |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-13T05:04:13Z |
| publishDate | 2009-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-1be9977df27f45ce8a7cdf07aa5090dc2022-12-22T03:01:14ZengMDPI AGMolecules1420-30492009-10-0114104197421210.3390/molecules14104197Rhodanineacetic Acid Derivatives as Potential Drugs: Preparation, Hydrophobic Properties and Antifungal Activity of (5-Arylalkylidene-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)acetic AcidsJosef JampilekJiri KunesVejsova MarcelaPetra HirsovaJiri DohnalVeronika OpletalovaJan DolezelSome [(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.http://www.mdpi.com/1420-3049/14/10/4197/[(5Z)-(5-arylalkylidene-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)]acetic acidssynthesislipophilicity measurementin vitro antifungal activity |
| spellingShingle | Josef Jampilek Jiri Kunes Vejsova Marcela Petra Hirsova Jiri Dohnal Veronika Opletalova Jan Dolezel 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 [(5Z)-(5-arylalkylidene-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)]acetic acids synthesis lipophilicity measurement in vitro antifungal activity |
| title | 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 |
| title_full | 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 |
| title_fullStr | 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 |
| title_full_unstemmed | 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 |
| title_short | 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 |
| title_sort | 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 |
| topic | [(5Z)-(5-arylalkylidene-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)]acetic acids synthesis lipophilicity measurement in vitro antifungal activity |
| url | http://www.mdpi.com/1420-3049/14/10/4197/ |
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