Tandem Thio-Michael Addition/Remote Lactone Activation of 5-Hydroxymethylfurfural-Derived δ-Lactone-Fused Cyclopentenones

Detalhes bibliográficos
Autor(a) principal: Rafael, Rafael F.
Data de Publicação: 2022
Outros Autores: Ravasco, Joao M.J.M., Andrade, Késsia H.S., Coelho, Jaime A.S., Moreira, Rui, Oliveira, Rafael, Nogueira, Fátima, Afonso, Carlos A.M.
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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spelling 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:RCAAP2024-03-11T05:30:15Zoai:run.unl.pt:10362/148588Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T03:53:25.637232Repositório 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
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
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instacron:RCAAP
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
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reponame_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
collection Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository.name.fl_str_mv Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
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