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Synthesis of new 3-acetyl-1,3,4-oxadiazolines combined with pyrimidines as antileishmanial and antiviral agents
A new series of 3-acetyl-1,3,4-oxadiazoline hybrid molecules was designed and synthesized using a condensation between acyclonucleosides and substituted phenylhydrazone. All intermediates and final products were screened against Leishmania donovani, a Protozoan parasite and against three viruses SAR...
Autores principales: | , , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Springer International Publishing
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9573813/ https://www.ncbi.nlm.nih.gov/pubmed/36251201 http://dx.doi.org/10.1007/s11030-022-10548-9 |
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author | Lachhab, Saida El Mansouri, Az-eddine Mehdi, Ahmad Dennemont, Indira Neyts, Johan Jochmans, Dirk Andrei, Graciela Snoeck, Robert Sanghvi, Yogesh S. Ait Ali, Mustapha Loiseau, Philippe M. Lazrek, Hassan B. |
author_facet | Lachhab, Saida El Mansouri, Az-eddine Mehdi, Ahmad Dennemont, Indira Neyts, Johan Jochmans, Dirk Andrei, Graciela Snoeck, Robert Sanghvi, Yogesh S. Ait Ali, Mustapha Loiseau, Philippe M. Lazrek, Hassan B. |
author_sort | Lachhab, Saida |
collection | PubMed |
description | A new series of 3-acetyl-1,3,4-oxadiazoline hybrid molecules was designed and synthesized using a condensation between acyclonucleosides and substituted phenylhydrazone. All intermediates and final products were screened against Leishmania donovani, a Protozoan parasite and against three viruses SARS-CoV-2, HCMV and VZV. While no significant activity was observed against the viruses, the intermediate with 6-azatymine as thymine and 5-azathymine-3-acetyl-1,3,4-oxadiazoline hybrid exhibited a significant antileishmanial activity. The later compound was the most promising, exhibiting an IC(50) value at 8.98 µM on L. donovani intramacrophage amastigotes and a moderate selectivity index value at 2.4. GRAPHICAL ABSTRACT: [Image: see text] SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1007/s11030-022-10548-9. |
format | Online Article Text |
id | pubmed-9573813 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | Springer International Publishing |
record_format | MEDLINE/PubMed |
spelling | pubmed-95738132022-10-17 Synthesis of new 3-acetyl-1,3,4-oxadiazolines combined with pyrimidines as antileishmanial and antiviral agents Lachhab, Saida El Mansouri, Az-eddine Mehdi, Ahmad Dennemont, Indira Neyts, Johan Jochmans, Dirk Andrei, Graciela Snoeck, Robert Sanghvi, Yogesh S. Ait Ali, Mustapha Loiseau, Philippe M. Lazrek, Hassan B. Mol Divers Original Article A new series of 3-acetyl-1,3,4-oxadiazoline hybrid molecules was designed and synthesized using a condensation between acyclonucleosides and substituted phenylhydrazone. All intermediates and final products were screened against Leishmania donovani, a Protozoan parasite and against three viruses SARS-CoV-2, HCMV and VZV. While no significant activity was observed against the viruses, the intermediate with 6-azatymine as thymine and 5-azathymine-3-acetyl-1,3,4-oxadiazoline hybrid exhibited a significant antileishmanial activity. The later compound was the most promising, exhibiting an IC(50) value at 8.98 µM on L. donovani intramacrophage amastigotes and a moderate selectivity index value at 2.4. GRAPHICAL ABSTRACT: [Image: see text] SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1007/s11030-022-10548-9. Springer International Publishing 2022-10-17 /pmc/articles/PMC9573813/ /pubmed/36251201 http://dx.doi.org/10.1007/s11030-022-10548-9 Text en © The Author(s), under exclusive licence to Springer Nature Switzerland AG 2022, Springer Nature or its licensor holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law. This article is made available via the PMC Open Access Subset for unrestricted research re-use and secondary analysis in any form or by any means with acknowledgement of the original source. These permissions are granted for the duration of the World Health Organization (WHO) declaration of COVID-19 as a global pandemic. |
spellingShingle | Original Article Lachhab, Saida El Mansouri, Az-eddine Mehdi, Ahmad Dennemont, Indira Neyts, Johan Jochmans, Dirk Andrei, Graciela Snoeck, Robert Sanghvi, Yogesh S. Ait Ali, Mustapha Loiseau, Philippe M. Lazrek, Hassan B. Synthesis of new 3-acetyl-1,3,4-oxadiazolines combined with pyrimidines as antileishmanial and antiviral agents |
title | Synthesis of new 3-acetyl-1,3,4-oxadiazolines combined with pyrimidines as antileishmanial and antiviral agents |
title_full | Synthesis of new 3-acetyl-1,3,4-oxadiazolines combined with pyrimidines as antileishmanial and antiviral agents |
title_fullStr | Synthesis of new 3-acetyl-1,3,4-oxadiazolines combined with pyrimidines as antileishmanial and antiviral agents |
title_full_unstemmed | Synthesis of new 3-acetyl-1,3,4-oxadiazolines combined with pyrimidines as antileishmanial and antiviral agents |
title_short | Synthesis of new 3-acetyl-1,3,4-oxadiazolines combined with pyrimidines as antileishmanial and antiviral agents |
title_sort | synthesis of new 3-acetyl-1,3,4-oxadiazolines combined with pyrimidines as antileishmanial and antiviral agents |
topic | Original Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9573813/ https://www.ncbi.nlm.nih.gov/pubmed/36251201 http://dx.doi.org/10.1007/s11030-022-10548-9 |
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