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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...
Autores principales: | , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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MDPI
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9268742/ https://www.ncbi.nlm.nih.gov/pubmed/35807224 http://dx.doi.org/10.3390/molecules27133975 |
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author | Żesławska, Ewa Zakrzewski, Robert Nowicki, Arkadiusz Korona-Głowniak, Izabela Lyčka, Antonín Kania, Agnieszka Zborowski, Krzysztof Kazimierz Suder, Piotr Skórska-Stania, Agnieszka Tejchman, Waldemar |
author_facet | Żesławska, Ewa Zakrzewski, Robert Nowicki, Arkadiusz Korona-Głowniak, Izabela Lyčka, Antonín Kania, Agnieszka Zborowski, Krzysztof Kazimierz Suder, Piotr Skórska-Stania, Agnieszka Tejchman, Waldemar |
author_sort | Żesławska, Ewa |
collection | PubMed |
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. |
format | Online Article Text |
id | pubmed-9268742 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-92687422022-07-09 Synthesis, Crystal Structures, Lipophilic Properties and Antimicrobial Activity of 5-Pyridylmethylidene-3-rhodanine-carboxyalkyl Acids Derivatives Żesławska, Ewa Zakrzewski, Robert Nowicki, Arkadiusz Korona-Głowniak, Izabela Lyčka, Antonín Kania, Agnieszka Zborowski, Krzysztof Kazimierz Suder, Piotr Skórska-Stania, Agnieszka Tejchman, Waldemar Molecules Article 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. MDPI 2022-06-21 /pmc/articles/PMC9268742/ /pubmed/35807224 http://dx.doi.org/10.3390/molecules27133975 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Żesławska, Ewa Zakrzewski, Robert Nowicki, Arkadiusz Korona-Głowniak, Izabela Lyčka, Antonín Kania, Agnieszka Zborowski, Krzysztof Kazimierz Suder, Piotr Skórska-Stania, Agnieszka Tejchman, Waldemar Synthesis, Crystal Structures, Lipophilic Properties and Antimicrobial Activity of 5-Pyridylmethylidene-3-rhodanine-carboxyalkyl Acids Derivatives |
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 | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9268742/ https://www.ncbi.nlm.nih.gov/pubmed/35807224 http://dx.doi.org/10.3390/molecules27133975 |
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