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 <i>C</i>-(diethoxyphosphonyl)nitrones with <i>N</i><sup>3</sup>-allyl-<i>N</i><sup>1</sup>-benzylquinazoline-2,4-diones produced mixtures of diastereoisomeric 3-(diethoxyphosphonyl)isoxazolidines w...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/19/6526 |
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| author | Magdalena Łysakowska Iwona E. Głowacka Graciela Andrei Dominique Schols Robert Snoeck Paweł Lisiecki Magdalena Szemraj Dorota G. Piotrowska |
| author_facet | Magdalena Łysakowska Iwona E. Głowacka Graciela Andrei Dominique Schols Robert Snoeck Paweł Lisiecki Magdalena Szemraj Dorota G. Piotrowska |
| author_sort | Magdalena Łysakowska |
| collection | DOAJ |
| description | Dipolar cycloaddition of the N-substituted <i>C</i>-(diethoxyphosphonyl)nitrones with <i>N</i><sup>3</sup>-allyl-<i>N</i><sup>1</sup>-benzylquinazoline-2,4-diones produced mixtures of diastereoisomeric 3-(diethoxyphosphonyl)isoxazolidines with a <i>N</i><sup>1</sup>-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<sub>50</sub> values in the range of 12.63–58.48 µM. A mixture of isoxazolidines <i>cis</i>-<b>20c</b>/<i>trans</i>-<b>20c</b> (6:94) was found to be the most active against <i>B. cereus</i> PCM 1948, showing an MIC value 0.625 mg/mL, and also was not mutagenic up to this concentration. |
| first_indexed | 2024-03-09T21:24:47Z |
| format | Article |
| id | doaj.art-8b6be0e2e6704e748d8d5ae29adf2ad9 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T21:24:47Z |
| publishDate | 2022-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-8b6be0e2e6704e748d8d5ae29adf2ad92023-11-23T21:12:49ZengMDPI AGMolecules1420-30492022-10-012719652610.3390/molecules27196526Design, Synthesis, Anti-Varicella-Zoster and Antimicrobial Activity of (Isoxazolidin-3-yl)Phosphonate Conjugates of N1-Functionalised Quinazoline-2,4-DionesMagdalena Łysakowska0Iwona E. Głowacka1Graciela Andrei2Dominique Schols3Robert Snoeck4Paweł Lisiecki5Magdalena Szemraj6Dorota G. Piotrowska7Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Lodz, Muszynskiego 1, 90-151 Lodz, PolandBioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Lodz, Muszynskiego 1, 90-151 Lodz, PolandLaboratory of Virology and Chemotherapy, Rega Institute, Department of Microbiology, Immunology and Transplantation, KU Leuven, B-3000 Leuven, BelgiumLaboratory of Virology and Chemotherapy, Rega Institute, Department of Microbiology, Immunology and Transplantation, KU Leuven, B-3000 Leuven, BelgiumLaboratory of Virology and Chemotherapy, Rega Institute, Department of Microbiology, Immunology and Transplantation, KU Leuven, B-3000 Leuven, BelgiumDepartment of Pharmaceutical Microbiology and Microbiological Diagnostics, Faculty of Pharmacy, Medical University of Lodz, Muszynskiego 1, 90-151 Lodz, PolandDepartment of Pharmaceutical Microbiology and Microbiological Diagnostics, Faculty of Pharmacy, Medical University of Lodz, Muszynskiego 1, 90-151 Lodz, PolandBioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Lodz, Muszynskiego 1, 90-151 Lodz, PolandDipolar cycloaddition of the N-substituted <i>C</i>-(diethoxyphosphonyl)nitrones with <i>N</i><sup>3</sup>-allyl-<i>N</i><sup>1</sup>-benzylquinazoline-2,4-diones produced mixtures of diastereoisomeric 3-(diethoxyphosphonyl)isoxazolidines with a <i>N</i><sup>1</sup>-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<sub>50</sub> values in the range of 12.63–58.48 µM. A mixture of isoxazolidines <i>cis</i>-<b>20c</b>/<i>trans</i>-<b>20c</b> (6:94) was found to be the most active against <i>B. cereus</i> PCM 1948, showing an MIC value 0.625 mg/mL, and also was not mutagenic up to this concentration.https://www.mdpi.com/1420-3049/27/19/6526isoxazolidinesquinazoline-2,4-dionesphosphonatesantiviral activityantimicrobial activity |
| spellingShingle | Magdalena Łysakowska Iwona E. Głowacka Graciela Andrei Dominique Schols Robert Snoeck Paweł Lisiecki Magdalena Szemraj Dorota G. Piotrowska Design, Synthesis, Anti-Varicella-Zoster and Antimicrobial Activity of (Isoxazolidin-3-yl)Phosphonate Conjugates of N1-Functionalised Quinazoline-2,4-Diones Molecules isoxazolidines quinazoline-2,4-diones phosphonates antiviral activity antimicrobial activity |
| 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 | isoxazolidines quinazoline-2,4-diones phosphonates antiviral activity antimicrobial activity |
| url | https://www.mdpi.com/1420-3049/27/19/6526 |
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