Synthesis, Crystal Structures, Lipophilic Properties and Antimicrobial Activity of 5-Pyridylmethylidene-3-rhodanine-carboxyalkyl Acids Derivatives
The constant increase in the resistance of pathogenic bacteria to the commonly used drugs so far makes it necessary to search for new substances with antibacterial activity. Taking up this challenge, we obtained a series of rhodanine-3-carboxyalkyl acid derivatives containing 2- or 3- or 4-pyridinyl...
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MDPI AG
2022-06-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/13/3975 |
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| author | Ewa Żesławska Robert Zakrzewski Arkadiusz Nowicki Izabela Korona-Głowniak Antonín Lyčka Agnieszka Kania Krzysztof Kazimierz Zborowski Piotr Suder Agnieszka Skórska-Stania Waldemar Tejchman |
| author_facet | Ewa Żesławska Robert Zakrzewski Arkadiusz Nowicki Izabela Korona-Głowniak Antonín Lyčka Agnieszka Kania Krzysztof Kazimierz Zborowski Piotr Suder Agnieszka Skórska-Stania Waldemar Tejchman |
| author_sort | Ewa Żesławska |
| collection | DOAJ |
| description | The constant increase in the resistance of pathogenic bacteria to the commonly used drugs so far makes it necessary to search for new substances with antibacterial activity. Taking up this challenge, we obtained a series of rhodanine-3-carboxyalkyl acid derivatives containing 2- or 3- or 4-pyridinyl moiety at the C-5 position. These compounds were tested for their antibacterial and antifungal activities. They showed activity against Gram-positive bacteria while they were inactive against Gram-negative bacteria and yeast. In order to explain the relationship between the activity of the compounds and their structure, for selected derivatives crystal structures were determined using the X-ray diffraction method. Modeling of the isosurface of electron density was also performed. For all tested compounds their lipophilicity was determined by the RP-TLC method and by calculation methods. On the basis of the carried-out research, it was found that the derivatives with 1.5 N···S electrostatics interactions between the nitrogen atom in the pyridine moiety and the sulfur atom in the rhodanine system showed the highest biological activity. |
| first_indexed | 2024-03-09T04:02:03Z |
| format | Article |
| id | doaj.art-f805d508317f44339a3cdae6f6416687 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T04:02:03Z |
| publishDate | 2022-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-f805d508317f44339a3cdae6f64166872023-12-03T14:12:43ZengMDPI AGMolecules1420-30492022-06-012713397510.3390/molecules27133975Synthesis, Crystal Structures, Lipophilic Properties and Antimicrobial Activity of 5-Pyridylmethylidene-3-rhodanine-carboxyalkyl Acids DerivativesEwa Żesławska0Robert Zakrzewski1Arkadiusz Nowicki2Izabela Korona-Głowniak3Antonín Lyčka4Agnieszka Kania5Krzysztof Kazimierz Zborowski6Piotr Suder7Agnieszka Skórska-Stania8Waldemar Tejchman9Institute of Biology, Pedagogical University of Krakow, Podchorążych 2, 30-084 Kraków, PolandFaculty of Chemistry, University of Lodz, Tamka 12, 91-403 Łódź, PolandFaculty of Chemistry, University of Lodz, Tamka 12, 91-403 Łódź, PolandDepartment of Pharmaceutical Microbiology, Medical University of Lublin, Chodźki 1, 20-093 Lublin, PolandDepartment of Chemistry, University of Hradec Králové, Rokitanského 62, 500 03 Hradec Králové III, Czech RepublicInstitute of Biology, Pedagogical University of Krakow, Podchorążych 2, 30-084 Kraków, PolandFaculty of Chemistry, Jagiellonian University in Kraków, Gronostajowa 2, 30-387 Kraków, PolandDepartment of Analytical Chemistry and Biochemistry, Faculty of Materials Science and Ceramics, AGH University of Science and Technology, Mickiewicza 30, 30-059 Kraków, PolandFaculty of Chemistry, Jagiellonian University in Kraków, Gronostajowa 2, 30-387 Kraków, PolandInstitute of Biology, Pedagogical University of Krakow, Podchorążych 2, 30-084 Kraków, PolandThe constant increase in the resistance of pathogenic bacteria to the commonly used drugs so far makes it necessary to search for new substances with antibacterial activity. Taking up this challenge, we obtained a series of rhodanine-3-carboxyalkyl acid derivatives containing 2- or 3- or 4-pyridinyl moiety at the C-5 position. These compounds were tested for their antibacterial and antifungal activities. They showed activity against Gram-positive bacteria while they were inactive against Gram-negative bacteria and yeast. In order to explain the relationship between the activity of the compounds and their structure, for selected derivatives crystal structures were determined using the X-ray diffraction method. Modeling of the isosurface of electron density was also performed. For all tested compounds their lipophilicity was determined by the RP-TLC method and by calculation methods. On the basis of the carried-out research, it was found that the derivatives with 1.5 N···S electrostatics interactions between the nitrogen atom in the pyridine moiety and the sulfur atom in the rhodanine system showed the highest biological activity.https://www.mdpi.com/1420-3049/27/13/3975rhodanineantimicrobial activitylipophilicitycrystal structureelectron densityN···S interaction |
| spellingShingle | Ewa Żesławska Robert Zakrzewski Arkadiusz Nowicki Izabela Korona-Głowniak Antonín Lyčka Agnieszka Kania Krzysztof Kazimierz Zborowski Piotr Suder Agnieszka Skórska-Stania Waldemar Tejchman Synthesis, Crystal Structures, Lipophilic Properties and Antimicrobial Activity of 5-Pyridylmethylidene-3-rhodanine-carboxyalkyl Acids Derivatives Molecules rhodanine antimicrobial activity lipophilicity crystal structure electron density N···S interaction |
| title | Synthesis, Crystal Structures, Lipophilic Properties and Antimicrobial Activity of 5-Pyridylmethylidene-3-rhodanine-carboxyalkyl Acids Derivatives |
| title_full | Synthesis, Crystal Structures, Lipophilic Properties and Antimicrobial Activity of 5-Pyridylmethylidene-3-rhodanine-carboxyalkyl Acids Derivatives |
| title_fullStr | Synthesis, Crystal Structures, Lipophilic Properties and Antimicrobial Activity of 5-Pyridylmethylidene-3-rhodanine-carboxyalkyl Acids Derivatives |
| title_full_unstemmed | Synthesis, Crystal Structures, Lipophilic Properties and Antimicrobial Activity of 5-Pyridylmethylidene-3-rhodanine-carboxyalkyl Acids Derivatives |
| title_short | Synthesis, Crystal Structures, Lipophilic Properties and Antimicrobial Activity of 5-Pyridylmethylidene-3-rhodanine-carboxyalkyl Acids Derivatives |
| title_sort | synthesis crystal structures lipophilic properties and antimicrobial activity of 5 pyridylmethylidene 3 rhodanine carboxyalkyl acids derivatives |
| topic | rhodanine antimicrobial activity lipophilicity crystal structure electron density N···S interaction |
| url | https://www.mdpi.com/1420-3049/27/13/3975 |
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