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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Detalles Bibliográficos
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
Descripción
Sumario: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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