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http://hdl.handle.net/10773/36109
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DC Field | Value | Language |
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dc.contributor.author | Sousa, Joana L. C. | pt_PT |
dc.contributor.author | Albuquerque, Hélio M. T. | pt_PT |
dc.contributor.author | Silvestre, Armando J. D. | pt_PT |
dc.contributor.author | Silva, Artur M. S. | pt_PT |
dc.date.accessioned | 2023-01-30T13:03:29Z | - |
dc.date.available | 2023-01-30T13:03:29Z | - |
dc.date.issued | 2022-08 | - |
dc.identifier.uri | http://hdl.handle.net/10773/36109 | - |
dc.description.abstract | Betulinic acid (BA) was used as starting building block to create a library of novel BA-derived compounds containing O- and N-heterocycles. Firstly, BA was converted into methyl betulonate (BoOMe), which was used as intermediate in the developed methodologies. 1,2-Oxazine-fused BoOMe compounds were obtained in 12–25% global yields through a Michael addition of nitromethane to methyl (E)-2-benzylidenebetulonate derivatives, followed by nitro group reduction and intramolecular cyclization. Remarkably, the triterpene acts as a diastereoselective inducer in the conjugate addition of nitromethane, originating only one diastereomer out of four possible ones. Furthermore, other oxygen and nitrogen-containing heterocycles were installed at the A-ring of BoOMe, affording 2-amino-3-cyano-4H-pyran-fused BoOMe, diarylpyridine-fused BoOMe and 1,2,3-triazole–BoOMe compounds, using simple and straightforward synthetic methodologies. Finally, BA was revealed to be a versatile starting material, allowing the creation of a molecular diversification of compounds containing a triterpenic scaffold and O- and N-heterocycles. | pt_PT |
dc.language.iso | eng | pt_PT |
dc.publisher | MDPI | pt_PT |
dc.relation | POCI-01-0145-FEDER-016403 | pt_PT |
dc.relation | info:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F50011%2F2020/PT | pt_PT |
dc.relation | info:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP%2F50011%2F2020/PT | pt_PT |
dc.relation | info:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F50006%2F2020/PT | pt_PT |
dc.relation | POCI-01-0145-FEDER-029767 | pt_PT |
dc.rights | openAccess | pt_PT |
dc.rights.uri | https://creativecommons.org/licenses/by/4.0/ | pt_PT |
dc.subject | Triterpenoids | pt_PT |
dc.subject | Betulinic acid | pt_PT |
dc.subject | Oxygen heterocycles | pt_PT |
dc.subject | Nitrogen heterocycles | pt_PT |
dc.subject | Diastereoselectivity | pt_PT |
dc.subject | Michael addition | pt_PT |
dc.title | Decoration of A-ring of a lupane-type triterpenoid with different oxygen and nitrogen heterocycles | pt_PT |
dc.type | article | pt_PT |
dc.description.version | published | pt_PT |
dc.peerreviewed | yes | pt_PT |
degois.publication.issue | 15 | pt_PT |
degois.publication.title | Molecules | pt_PT |
degois.publication.volume | 27 | pt_PT |
dc.relation.publisherversion | https://www.mdpi.com/1420-3049/27/15/4904 | pt_PT |
dc.identifier.doi | 10.3390/molecules27154904 | pt_PT |
dc.identifier.essn | 1420-3049 | pt_PT |
dc.identifier.articlenumber | 4904 | pt_PT |
Appears in Collections: | CICECO - Artigos DQ - Artigos REQUIMTE - Artigos |
Files in This Item:
File | Description | Size | Format | |
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molecules-27-04904.pdf | 2.36 MB | Adobe PDF | View/Open |
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