Tandem Thio-Michael Addition/Remote Lactone Activation of 5-Hydroxymethylfurfural-Derived δ-Lactone-Fused Cyclopentenones
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2022 |
| 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/10362/148588 |
Resumo: | Funding Information: We thank the Fundação para a Ciência e a Tecnologia (SFRH/BD/120829/2016, SFRH/BD/148211/2019, UIDB/04138/2020, UIDP/04138/2020, PTDC/QUI‐QOR/32008/2017 and GHTM‐UID/04413/2020). The project leading to this application has received funding from the European Union's Horizon 2020 research and innovation programme under grant agreement No 951996. J. A. S. C. thanks the Fundação para a Ciência e a Tecnologia (FCT) for Scientific Employment Stimulus 2020/02383/CEECIND. Publisher Copyright: © 2022 The Authors. ChemSusChem published by Wiley-VCH GmbH. |
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Tandem Thio-Michael Addition/Remote Lactone Activation of 5-Hydroxymethylfurfural-Derived δ-Lactone-Fused Cyclopentenonesantimalarialbiomasscyclopentenonesfuranssustainable chemistryEnvironmental ChemistryChemical Engineering(all)Materials Science(all)Energy(all)Drug DiscoverySDG 3 - Good Health and Well-beingSDG 9 - Industry, Innovation, and InfrastructureSDG 11 - Sustainable Cities and CommunitiesFunding Information: We thank the Fundação para a Ciência e a Tecnologia (SFRH/BD/120829/2016, SFRH/BD/148211/2019, UIDB/04138/2020, UIDP/04138/2020, PTDC/QUI‐QOR/32008/2017 and GHTM‐UID/04413/2020). The project leading to this application has received funding from the European Union's Horizon 2020 research and innovation programme under grant agreement No 951996. J. A. S. C. thanks the Fundação para a Ciência e a Tecnologia (FCT) for Scientific Employment Stimulus 2020/02383/CEECIND. Publisher Copyright: © 2022 The Authors. ChemSusChem published by Wiley-VCH GmbH.The creation of structurally diverse chemical entities from fairly simple biorefinery products remains a challenge. In this work 5-hydroxymethylfurfural (HMF) was identified as a key synthon for preparing highly complex cyclopentenones (CP) via tandem 1,4-addition/elimination/remote lactone activation to external O- and N-nucleophiles in δ-lactone-fused-CPs hotspots. This scaffold was also reactive enough to be incorporated into model cysteine-peptides in low concentrations, paving the way to a potential translation generating complexity in the synthesis of small peptides. The new enones also exhibited activity against intraerythrocytic Plasmodium falciparum (IC50=1.32 μm).Global Health and Tropical Medicine (GHTM)Instituto de Higiene e Medicina Tropical (IHMT)Vector borne diseases and pathogens (VBD)RUNRafael, Rafael F.Ravasco, Joao M.J.M.Andrade, Késsia H.S.Coelho, Jaime A.S.Moreira, RuiOliveira, RafaelNogueira, FátimaAfonso, Carlos A.M.2023-02-02T22:20:05Z2022-07-072022-07-07T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10362/148588eng1864-5631PURE: 48275606https://doi.org/10.1002/cssc.202102204info: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:RCAAP2024-05-22T18:08:49Zoai:run.unl.pt:10362/148588Portal AgregadorONGhttps://www.rcaap.pt/oai/openairemluisa.alvim@gmail.comopendoar:71602024-05-22T18:08:49Repositório 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 |
Tandem Thio-Michael Addition/Remote Lactone Activation of 5-Hydroxymethylfurfural-Derived δ-Lactone-Fused Cyclopentenones |
| title |
Tandem Thio-Michael Addition/Remote Lactone Activation of 5-Hydroxymethylfurfural-Derived δ-Lactone-Fused Cyclopentenones |
| spellingShingle |
Tandem Thio-Michael Addition/Remote Lactone Activation of 5-Hydroxymethylfurfural-Derived δ-Lactone-Fused Cyclopentenones Rafael, Rafael F. antimalarial biomass cyclopentenones furans sustainable chemistry Environmental Chemistry Chemical Engineering(all) Materials Science(all) Energy(all) Drug Discovery SDG 3 - Good Health and Well-being SDG 9 - Industry, Innovation, and Infrastructure SDG 11 - Sustainable Cities and Communities |
| title_short |
Tandem Thio-Michael Addition/Remote Lactone Activation of 5-Hydroxymethylfurfural-Derived δ-Lactone-Fused Cyclopentenones |
| title_full |
Tandem Thio-Michael Addition/Remote Lactone Activation of 5-Hydroxymethylfurfural-Derived δ-Lactone-Fused Cyclopentenones |
| title_fullStr |
Tandem Thio-Michael Addition/Remote Lactone Activation of 5-Hydroxymethylfurfural-Derived δ-Lactone-Fused Cyclopentenones |
| title_full_unstemmed |
Tandem Thio-Michael Addition/Remote Lactone Activation of 5-Hydroxymethylfurfural-Derived δ-Lactone-Fused Cyclopentenones |
| title_sort |
Tandem Thio-Michael Addition/Remote Lactone Activation of 5-Hydroxymethylfurfural-Derived δ-Lactone-Fused Cyclopentenones |
| author |
Rafael, Rafael F. |
| author_facet |
Rafael, Rafael F. Ravasco, Joao M.J.M. Andrade, Késsia H.S. Coelho, Jaime A.S. Moreira, Rui Oliveira, Rafael Nogueira, Fátima Afonso, Carlos A.M. |
| author_role |
author |
| author2 |
Ravasco, Joao M.J.M. Andrade, Késsia H.S. Coelho, Jaime A.S. Moreira, Rui Oliveira, Rafael Nogueira, Fátima Afonso, Carlos A.M. |
| author2_role |
author author author author author author author |
| dc.contributor.none.fl_str_mv |
Global Health and Tropical Medicine (GHTM) Instituto de Higiene e Medicina Tropical (IHMT) Vector borne diseases and pathogens (VBD) RUN |
| dc.contributor.author.fl_str_mv |
Rafael, Rafael F. Ravasco, Joao M.J.M. Andrade, Késsia H.S. Coelho, Jaime A.S. Moreira, Rui Oliveira, Rafael Nogueira, Fátima Afonso, Carlos A.M. |
| dc.subject.por.fl_str_mv |
antimalarial biomass cyclopentenones furans sustainable chemistry Environmental Chemistry Chemical Engineering(all) Materials Science(all) Energy(all) Drug Discovery SDG 3 - Good Health and Well-being SDG 9 - Industry, Innovation, and Infrastructure SDG 11 - Sustainable Cities and Communities |
| topic |
antimalarial biomass cyclopentenones furans sustainable chemistry Environmental Chemistry Chemical Engineering(all) Materials Science(all) Energy(all) Drug Discovery SDG 3 - Good Health and Well-being SDG 9 - Industry, Innovation, and Infrastructure SDG 11 - Sustainable Cities and Communities |
| description |
Funding Information: We thank the Fundação para a Ciência e a Tecnologia (SFRH/BD/120829/2016, SFRH/BD/148211/2019, UIDB/04138/2020, UIDP/04138/2020, PTDC/QUI‐QOR/32008/2017 and GHTM‐UID/04413/2020). The project leading to this application has received funding from the European Union's Horizon 2020 research and innovation programme under grant agreement No 951996. J. A. S. C. thanks the Fundação para a Ciência e a Tecnologia (FCT) for Scientific Employment Stimulus 2020/02383/CEECIND. Publisher Copyright: © 2022 The Authors. ChemSusChem published by Wiley-VCH GmbH. |
| publishDate |
2022 |
| dc.date.none.fl_str_mv |
2022-07-07 2022-07-07T00:00:00Z 2023-02-02T22:20:05Z |
| 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/10362/148588 |
| url |
http://hdl.handle.net/10362/148588 |
| dc.language.iso.fl_str_mv |
eng |
| language |
eng |
| dc.relation.none.fl_str_mv |
1864-5631 PURE: 48275606 https://doi.org/10.1002/cssc.202102204 |
| dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
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openAccess |
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application/pdf |
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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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1817545914380713984 |