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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...

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Autores principales: Żesławska, Ewa, Zakrzewski, Robert, Nowicki, Arkadiusz, Korona-Głowniak, Izabela, Lyčka, Antonín, Kania, Agnieszka, Zborowski, Krzysztof Kazimierz, Suder, Piotr, Skórska-Stania, Agnieszka, Tejchman, Waldemar
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
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.
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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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