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Exploring the synthesis of aminal guanidine-based molecules

2024-03-18Artigo científico Acesso aberto
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dc.contributor.authorRippel, Rafael
dc.contributor.authorLeitão, Flávia
dc.contributor.authorGeorgieva, Miglena K.
dc.contributor.authorMamede, Rafael
dc.contributor.authorGomes, Clara S. B.
dc.contributor.authorRoma-Rodrigues, Catarina
dc.contributor.authorFernandes, Alexandra R.
dc.contributor.authorLourenço, Ana
dc.contributor.authorFerreira, Luísa M.
dc.contributor.authorBranco, Paula S.
dc.contributor.institutionDQ - Departamento de Química
dc.contributor.institutionLAQV@REQUIMTE
dc.contributor.institutionUCIBIO - Applied Molecular Biosciences Unit
dc.contributor.institutionDCV - Departamento de Ciências da Vida
dc.contributor.pblRSC - Royal Society of Chemistry
dc.date.accessioned2024-05-22T00:11:21Z
dc.date.available2024-05-22T00:11:21Z
dc.date.issued2024-03-18
dc.descriptionC. S. B. Gomes acknowledges the XTAL – Macromolecular Crystallography group (UCIBIO and i4HB) for granting access to the X-ray diffractometer. X-Ray infrastructure was financed by FCT-MCTES through project RECI/BBBBEP/0124/2012. Publisher Copyright: © 2024 The Royal Society of Chemistry.
dc.description.abstractA novel approach has been developed for the efficient synthesis of the unsymmetrical (2-aminopyrrolidin-1-yl)carboxamidine alkaloidal core found in cernumidine (1) and its analogs (20a, 20c, 20f, 20i-o). The key transformation in this process involves the utilization of the Curtius rearrangement, which plays a pivotal role in constructing the aminal moiety. One of the major challenges encountered during this synthesis was the instability of the free aminal core intermediate. Furthermore, a noteworthy observation during the synthesis was the racemization process that occurred during the isocyanate trapping by organometallic reagents. Detailed DFT calculations shed light on this phenomenon, revealing a neighboring coordination-induced mechanism. The resulting compounds were subjected to evaluation for their anti-inflammatory properties using lipopolysaccharide-stimulated human THP1 cells. Notably, compounds featuring the guanidine moiety and electron-donating groups exhibited significant anti-inflammatory activity. These findings suggest that these compounds hold promise as potential candidates for further development as anti-inflammatory agents.en
dc.description.versionpublishersversion
dc.description.versionpublished
dc.format.extent11
dc.format.extent2156574
dc.identifier.doi10.1039/d3nj05406c
dc.identifier.issn1144-0546
dc.identifier.otherPURE: 85886390
dc.identifier.otherPURE UUID: 1bc78714-4a3a-4e9f-9933-374e16d89979
dc.identifier.otherScopus: 85186993310
dc.identifier.otherWOS: 001176071500001
dc.identifier.otherORCID: /0000-0003-0839-4123/work/168299711
dc.identifier.otherORCID: /0000-0003-2054-4438/work/168299778
dc.identifier.otherORCID: /0000-0003-3672-0045/work/168299869
dc.identifier.otherORCID: /0000-0002-7312-8596/work/168300040
dc.identifier.otherORCID: /0000-0001-8474-3925/work/168300141
dc.identifier.otherORCID: /0000-0001-7358-3428/work/168300316
dc.identifier.urihttp://hdl.handle.net/10362/167645
dc.identifier.urlhttps://www.scopus.com/pages/publications/85186993310
dc.language.isoeng
dc.peerreviewedyes
dc.relationFunding Information: info:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/LA%2FP%2F0008%2F2020/PT
dc.relationinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP%2F50006%2F2020/PT
dc.relationAssociated Laboratory for Green Chemistry - Clean Technologies and Processes
dc.relationAssociated Laboratory for Green Chemistry - Clean Technologies and Processes
dc.relationApplied Molecular Biosciences Unit
dc.relationInstitute for Health and Bioeconomy
dc.relationA CHALLENGING GUANIDINE-BASED MOLECULE – THE SYNTHESIS AND ITS ACTION
dc.relationinfo:eu-repo/grantAgreement/FCT//SFRH%2FBD%2F136692%2F2018/PT
dc.subjectCatalysis
dc.subjectGeneral Chemistry
dc.subjectMaterials Chemistry
dc.titleExploring the synthesis of aminal guanidine-based moleculesen
dc.title.subtitlesynthesis of cernumidine and analogues, and survey of its anti-inflammatory activityen
dc.typejournal article
degois.publication.firstPage5247
degois.publication.issue12
degois.publication.lastPage5257
degois.publication.titleNew Journal of Chemistry
degois.publication.volume48
dspace.entity.typePublication
oaire.awardNumberUIDP/50006/2020
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oaire.awardNumberLA/P/0140/2020
oaire.awardNumberSFRH/BD/136692/2018
oaire.awardTitleAssociated Laboratory for Green Chemistry - Clean Technologies and Processes
oaire.awardTitleAssociated Laboratory for Green Chemistry - Clean Technologies and Processes
oaire.awardTitleApplied Molecular Biosciences Unit
oaire.awardTitleInstitute for Health and Bioeconomy
oaire.awardTitleA CHALLENGING GUANIDINE-BASED MOLECULE – THE SYNTHESIS AND ITS ACTION
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP%2F50006%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F50006%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP%2F04378%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/LA%2FP%2F0140%2F2020/PT
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oaire.fundingStream6817 - DCRRNI ID
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