Please use this identifier to cite or link to this item:
https://hdl.handle.net/10316/107467
DC Field | Value | Language |
---|---|---|
dc.contributor.author | Brandão, Pedro | - |
dc.contributor.author | Marques, Carolina | - |
dc.contributor.author | Pinto, Eugénia | - |
dc.contributor.author | Pineiro, Marta | - |
dc.contributor.author | Burke, Anthony J. | - |
dc.date.accessioned | 2023-07-13T10:54:02Z | - |
dc.date.available | 2023-07-13T10:54:02Z | - |
dc.date.issued | 2021 | - |
dc.identifier.issn | 1144-0546 | pt |
dc.identifier.issn | 1369-9261 | pt |
dc.identifier.uri | https://hdl.handle.net/10316/107467 | - |
dc.description.abstract | Tryptanthrin is a valuable tetracyclic alkaloid, which displays a wide variety of biological activities. The application of this type of scaffold as a starting material for the discovery of new drug candidates is of major importance in medicinal chemistry. In this work, we report one of the few examples of tryptanthrin-based multicomponent reaction approaches for drug discovery, and the first using the Petasis reaction. The optimized BINOL-catalyzed reaction conditions allowed the synthesis of a library of new tryptanthrin derivatives bearing considerable structural diversity. An asymmetric version was also established, achieving the desired enantiomerically pure derivative with 99% ee and 71% yield. The resulting library was screened against one Gram-positive and one Gram-negative bacteria, two yeasts, and three filamentous and four dermatophyte fungal strains with clinical relevance, with compound 5bea displaying moderate fungicidal activity. | pt |
dc.language.iso | eng | pt |
dc.publisher | Royal Society of Chemistry | pt |
dc.relation | info:eu-repo/grantAgreement/FCT/POR_CENTRO/PD/BD/128490/2017/PT/Sustainable Asymmetric Catalytic Synthesis of Novel Oxindole Hybrids with Potential Biological Activity | pt |
dc.relation | info:eu-repo/grantAgreement/FCT/UIDB/00313/2020 | pt |
dc.relation | info:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB/50006/2020/PT/Associated Laboratory for Green Chemistry - Clean Technologies and Processes | pt |
dc.relation | info:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB/04423/2020/PT/Interdisciplinary Centre of Marine and Environmental Research | pt |
dc.relation | info:eu-repo/grantAgreement/FCT/REEQ/481/QUI/2006 | pt |
dc.relation | info:eu-repo/grantAgreement/RECI/QEQ-QFI/0168/2012 | pt |
dc.relation | info:eu-repo/grantAgreement/CENTRO-07-CT62-FEDER-002012 | pt |
dc.rights | embargoedAccess | pt |
dc.rights.uri | http://creativecommons.org/licenses/by-nc-nd/4.0/ | pt |
dc.title | Petasis adducts of tryptanthrin – synthesis, biological activity evaluation and druglikeness assessment | pt |
dc.type | article | - |
degois.publication.firstPage | 14633 | pt |
degois.publication.lastPage | 14649 | pt |
degois.publication.issue | 32 | pt |
degois.publication.title | New Journal of Chemistry | pt |
dc.peerreviewed | yes | pt |
dc.identifier.doi | 10.1039/D1NJ02079J | pt |
degois.publication.volume | 45 | pt |
dc.date.embargo | 2022-01-01 | * |
uc.date.periodoEmbargo | 365 | pt |
item.grantfulltext | open | - |
item.cerifentitytype | Publications | - |
item.languageiso639-1 | en | - |
item.openairetype | article | - |
item.openairecristype | http://purl.org/coar/resource_type/c_18cf | - |
item.fulltext | Com Texto completo | - |
crisitem.author.researchunit | CQC - Coimbra Chemistry Centre | - |
crisitem.author.researchunit | CQC - Coimbra Chemistry Centre | - |
crisitem.author.parentresearchunit | Faculty of Sciences and Technology | - |
crisitem.author.parentresearchunit | Faculty of Sciences and Technology | - |
crisitem.author.orcid | 0000-0002-1455-7470 | - |
crisitem.author.orcid | 0000-0002-7460-3758 | - |
Appears in Collections: | I&D CQC - Artigos em Revistas Internacionais |
Files in This Item:
File | Description | Size | Format | |
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Brandao2021NewJChem.pdf | 3.98 MB | Adobe PDF | View/Open |
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