Design, Synthesis, Anti-Varicella-Zoster and Antimicrobial Activity of (Isoxazolidin-3-yl)Phosphonate Conjugates of N1-Functionalised Quinazoline-2,4-Diones

Dipolar cycloaddition of the N-substituted C-(diethoxyphosphonyl)nitrones with N(3)-allyl-N(1)-benzylquinazoline-2,4-diones produced mixtures of diastereoisomeric 3-(diethoxyphosphonyl)isoxazolidines with a N(1)-benzylquinazoline-2,4-dione unit at C5. The obtained compounds were assessed for antivir...

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Autores principales: Łysakowska, Magdalena, Głowacka, Iwona E., Andrei, Graciela, Schols, Dominique, Snoeck, Robert, Lisiecki, Paweł, Szemraj, Magdalena, Piotrowska, Dorota G.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9571433/
https://www.ncbi.nlm.nih.gov/pubmed/36235061
http://dx.doi.org/10.3390/molecules27196526
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author Łysakowska, Magdalena
Głowacka, Iwona E.
Andrei, Graciela
Schols, Dominique
Snoeck, Robert
Lisiecki, Paweł
Szemraj, Magdalena
Piotrowska, Dorota G.
author_facet Łysakowska, Magdalena
Głowacka, Iwona E.
Andrei, Graciela
Schols, Dominique
Snoeck, Robert
Lisiecki, Paweł
Szemraj, Magdalena
Piotrowska, Dorota G.
author_sort Łysakowska, Magdalena
collection PubMed
description Dipolar cycloaddition of the N-substituted C-(diethoxyphosphonyl)nitrones with N(3)-allyl-N(1)-benzylquinazoline-2,4-diones produced mixtures of diastereoisomeric 3-(diethoxyphosphonyl)isoxazolidines with a N(1)-benzylquinazoline-2,4-dione unit at C5. The obtained compounds were assessed for antiviral and antibacterial activities. Several compounds showed moderate inhibitory activities against VZV with EC(50) values in the range of 12.63–58.48 µM. A mixture of isoxazolidines cis-20c/trans-20c (6:94) was found to be the most active against B. cereus PCM 1948, showing an MIC value 0.625 mg/mL, and also was not mutagenic up to this concentration.
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spelling pubmed-95714332022-10-17 Design, Synthesis, Anti-Varicella-Zoster and Antimicrobial Activity of (Isoxazolidin-3-yl)Phosphonate Conjugates of N1-Functionalised Quinazoline-2,4-Diones Łysakowska, Magdalena Głowacka, Iwona E. Andrei, Graciela Schols, Dominique Snoeck, Robert Lisiecki, Paweł Szemraj, Magdalena Piotrowska, Dorota G. Molecules Article Dipolar cycloaddition of the N-substituted C-(diethoxyphosphonyl)nitrones with N(3)-allyl-N(1)-benzylquinazoline-2,4-diones produced mixtures of diastereoisomeric 3-(diethoxyphosphonyl)isoxazolidines with a N(1)-benzylquinazoline-2,4-dione unit at C5. The obtained compounds were assessed for antiviral and antibacterial activities. Several compounds showed moderate inhibitory activities against VZV with EC(50) values in the range of 12.63–58.48 µM. A mixture of isoxazolidines cis-20c/trans-20c (6:94) was found to be the most active against B. cereus PCM 1948, showing an MIC value 0.625 mg/mL, and also was not mutagenic up to this concentration. MDPI 2022-10-02 /pmc/articles/PMC9571433/ /pubmed/36235061 http://dx.doi.org/10.3390/molecules27196526 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
Łysakowska, Magdalena
Głowacka, Iwona E.
Andrei, Graciela
Schols, Dominique
Snoeck, Robert
Lisiecki, Paweł
Szemraj, Magdalena
Piotrowska, Dorota G.
Design, Synthesis, Anti-Varicella-Zoster and Antimicrobial Activity of (Isoxazolidin-3-yl)Phosphonate Conjugates of N1-Functionalised Quinazoline-2,4-Diones
title Design, Synthesis, Anti-Varicella-Zoster and Antimicrobial Activity of (Isoxazolidin-3-yl)Phosphonate Conjugates of N1-Functionalised Quinazoline-2,4-Diones
title_full Design, Synthesis, Anti-Varicella-Zoster and Antimicrobial Activity of (Isoxazolidin-3-yl)Phosphonate Conjugates of N1-Functionalised Quinazoline-2,4-Diones
title_fullStr Design, Synthesis, Anti-Varicella-Zoster and Antimicrobial Activity of (Isoxazolidin-3-yl)Phosphonate Conjugates of N1-Functionalised Quinazoline-2,4-Diones
title_full_unstemmed Design, Synthesis, Anti-Varicella-Zoster and Antimicrobial Activity of (Isoxazolidin-3-yl)Phosphonate Conjugates of N1-Functionalised Quinazoline-2,4-Diones
title_short Design, Synthesis, Anti-Varicella-Zoster and Antimicrobial Activity of (Isoxazolidin-3-yl)Phosphonate Conjugates of N1-Functionalised Quinazoline-2,4-Diones
title_sort design, synthesis, anti-varicella-zoster and antimicrobial activity of (isoxazolidin-3-yl)phosphonate conjugates of n1-functionalised quinazoline-2,4-diones
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9571433/
https://www.ncbi.nlm.nih.gov/pubmed/36235061
http://dx.doi.org/10.3390/molecules27196526
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