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Rejuvenating the [1, 2, 3]-triazolo [1,5-a]quinoxalin-4(5H)-one scaffold: synthesis and derivatization in a sustainable guise and preliminary antimicrobial evaluation

2023-03Journal article Open access
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dc.contributor.authorPelliccia, Sveva
dc.contributor.authorAlfano, Antonella Ilenia
dc.contributor.authorAssunção, Beatriz Ramos
dc.contributor.authorTurco, Luigia
dc.contributor.authorLembo, Francesca
dc.contributor.authorSumma, Vincenzo
dc.contributor.authorBuommino, Elisabetta
dc.contributor.authorBrindisi, Margherita
dc.date.accessioned2023-04-20T12:07:02Z
dc.date.available2023-04-20T12:07:02Z
dc.date.issued2023-03
dc.description.abstractThe [1,2,3]-triazolo [1,5-a] quinoxalin-4(5H)-one scaffold and its analogs triazole-fused heterocyclic compounds are relevant structural templates in both natural and synthetic biologically active compounds. However, their medicinal chemistry applications are often limited due to the lack of synthetic protocols combining straightforward generation of the central core while also allowing extensive decoration activity for drug discovery purposes. Herein, we report a "refreshed" synthesis of the [1,2,3]-triazolo [1,5-a]quinoxalin-4(5H)-one core, encompassing the use of eco-compatible catalysts and reaction conditions. We have also performed a sustainable and extensive derivatization campaign at both the endocyclic amide nitrogen and the ester functionality, comprehensively exploring the reaction scope and overcoming some of the previously reported difficulties in introducing functional groups on this structural template. Finally, we unveiled a preliminary biological investigation for the newly generated chemical entities. Our assessment of the compounds on different bacterial species (two S. aureus strains, three P. aeruginosa strains, K. pneumonia), and two fungal C. albicans strains, as well as the evaluation of their activity on S. epidermidis biofilm formation, foster further optimization for the retrieved hit compounds 9, 14, and 20.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationPelliccia S, Alfano AI, Assunção BR, Turco L, Lembo F, Summa V, et al. Rejuvenating the [1, 2, 3]-triazolo [1,5-a]quinoxalin-4(5 H)-one scaffold: synthesis and derivatization in a sustainable guise and preliminary antimicrobial evaluation. Front Chem. 2023;11:1126427.pt_PT
dc.identifier.doi10.3389/fchem.2023.1126427pt_PT
dc.identifier.urihttp://hdl.handle.net/10400.21/15918
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherFrontiers Mediapt_PT
dc.relation.publisherversionhttps://www.frontiersin.org/articles/10.3389/fchem.2023.1126427/fullpt_PT
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/pt_PT
dc.subjectTriazolopt_PT
dc.subjectQuinoxalinpt_PT
dc.subjectAntimicrobial agentspt_PT
dc.subjectDrug discoverypt_PT
dc.subjectGreen chemistrypt_PT
dc.subjectPrivileged scaffoldpt_PT
dc.subjectSustainable synthesispt_PT
dc.titleRejuvenating the [1, 2, 3]-triazolo [1,5-a]quinoxalin-4(5H)-one scaffold: synthesis and derivatization in a sustainable guise and preliminary antimicrobial evaluationpt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.citation.startPage1126427pt_PT
oaire.citation.titleFrontiers in Chemistrypt_PT
oaire.citation.volume11pt_PT
rcaap.rightsopenAccesspt_PT
rcaap.typearticlept_PT

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