Exploring the synthesis of aminal guanidine-based molecules
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2024 |
| Outros Autores: | , , , , , , , , |
| Tipo de documento: | Artigo |
| Idioma: | eng |
| Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
| Texto Completo: | http://hdl.handle.net/10362/167645 |
Resumo: | C. 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. |
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Exploring the synthesis of aminal guanidine-based moleculessynthesis of cernumidine and analogues, and survey of its anti-inflammatory activityCatalysisChemistry(all)Materials ChemistryC. 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.A 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.DQ - Departamento de QuímicaLAQV@REQUIMTEUCIBIO - Applied Molecular Biosciences UnitDCV - Departamento de Ciências da VidaRUNRippel, RafaelLeitão, FláviaGeorgieva, Miglena K.Mamede, RafaelGomes, Clara S. B.Roma-Rodrigues, CatarinaFernandes, Alexandra R.Lourenço, AnaFerreira, Luísa M.Branco, Paula S.2024-05-22T00:11:21Z2024-03-182024-03-18T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article11application/pdfhttp://hdl.handle.net/10362/167645eng1144-0546PURE: 85886390https://doi.org/10.1039/d3nj05406cinfo:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2024-09-30T01:40:05Zoai:run.unl.pt:10362/167645Portal AgregadorONGhttps://www.rcaap.pt/oai/openairemluisa.alvim@gmail.comopendoar:71602024-09-30T01:40:05Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse |
| dc.title.none.fl_str_mv |
Exploring the synthesis of aminal guanidine-based molecules synthesis of cernumidine and analogues, and survey of its anti-inflammatory activity |
| title |
Exploring the synthesis of aminal guanidine-based molecules |
| spellingShingle |
Exploring the synthesis of aminal guanidine-based molecules Rippel, Rafael Catalysis Chemistry(all) Materials Chemistry |
| title_short |
Exploring the synthesis of aminal guanidine-based molecules |
| title_full |
Exploring the synthesis of aminal guanidine-based molecules |
| title_fullStr |
Exploring the synthesis of aminal guanidine-based molecules |
| title_full_unstemmed |
Exploring the synthesis of aminal guanidine-based molecules |
| title_sort |
Exploring the synthesis of aminal guanidine-based molecules |
| author |
Rippel, Rafael |
| author_facet |
Rippel, Rafael Leitão, Flávia Georgieva, Miglena K. Mamede, Rafael Gomes, Clara S. B. Roma-Rodrigues, Catarina Fernandes, Alexandra R. Lourenço, Ana Ferreira, Luísa M. Branco, Paula S. |
| author_role |
author |
| author2 |
Leitão, Flávia Georgieva, Miglena K. Mamede, Rafael Gomes, Clara S. B. Roma-Rodrigues, Catarina Fernandes, Alexandra R. Lourenço, Ana Ferreira, Luísa M. Branco, Paula S. |
| author2_role |
author author author author author author author author author |
| dc.contributor.none.fl_str_mv |
DQ - Departamento de Química LAQV@REQUIMTE UCIBIO - Applied Molecular Biosciences Unit DCV - Departamento de Ciências da Vida RUN |
| dc.contributor.author.fl_str_mv |
Rippel, Rafael Leitão, Flávia Georgieva, Miglena K. Mamede, Rafael Gomes, Clara S. B. Roma-Rodrigues, Catarina Fernandes, Alexandra R. Lourenço, Ana Ferreira, Luísa M. Branco, Paula S. |
| dc.subject.por.fl_str_mv |
Catalysis Chemistry(all) Materials Chemistry |
| topic |
Catalysis Chemistry(all) Materials Chemistry |
| description |
C. 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. |
| publishDate |
2024 |
| dc.date.none.fl_str_mv |
2024-05-22T00:11:21Z 2024-03-18 2024-03-18T00:00:00Z |
| dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
| dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
| format |
article |
| status_str |
publishedVersion |
| dc.identifier.uri.fl_str_mv |
http://hdl.handle.net/10362/167645 |
| url |
http://hdl.handle.net/10362/167645 |
| dc.language.iso.fl_str_mv |
eng |
| language |
eng |
| dc.relation.none.fl_str_mv |
1144-0546 PURE: 85886390 https://doi.org/10.1039/d3nj05406c |
| dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
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openAccess |
| dc.format.none.fl_str_mv |
11 application/pdf |
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reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação instacron:RCAAP |
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Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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RCAAP |
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RCAAP |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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mluisa.alvim@gmail.com |
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1817546016837074944 |