Synthesis and Antiproliferative Activity of Novel Quercetin-1,2,3- Triazole Hybrids using the 1,3-Dipolar Cycloaddition (Click) Reaction
Autor(a) principal: | |
---|---|
Data de Publicação: | 2022 |
Outros Autores: | , |
Tipo de documento: | Artigo |
Idioma: | por |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | http://hdl.handle.net/10174/34077 https://doi.org/10.1055/s-0040-1719928 |
Resumo: | Twenty-three new quercetin-1,2,3-triazole hybrids were synthesized in good to quantitative yields via Cu(I)-catalyzed azide- alkyne cycloaddition reaction under microwave irradiation. These new hybrids contain a 1,4-disubstituted 1,2,3-triazole ring at the 3-OH posi- tion of quercetin whilst the remaining hydroxyl groups were either pro- tected as methyl or benzyl groups or left unprotected. All the querce- tin-1,2,3-triazole hybrids I–IV were evaluated against REM-134 canine mammary cancer cell line, which is used as a translational model for hu- man breast cancer. These new analogues exhibit potent antiprolifera- tive activity against this cancer cell line. Furthermore, the results show that some of the new quercetin-1,2,3-triazole hybrids have better activ- ity than quercetin. Our best inhibitors displayed IC50 values in the range of 41–180 nM, and undoubtedly will have an important impact on the treatment of both canine and human breast cancer. |
id |
RCAP_3086a7a8c38968f6caa2f810d3f9883c |
---|---|
oai_identifier_str |
oai:dspace.uevora.pt:10174/34077 |
network_acronym_str |
RCAP |
network_name_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
repository_id_str |
7160 |
spelling |
Synthesis and Antiproliferative Activity of Novel Quercetin-1,2,3- Triazole Hybrids using the 1,3-Dipolar Cycloaddition (Click) Reaction1,2,3-triazoleQuercetinHuisgen reactionmolecular hybridizationanticancerflavonoidTwenty-three new quercetin-1,2,3-triazole hybrids were synthesized in good to quantitative yields via Cu(I)-catalyzed azide- alkyne cycloaddition reaction under microwave irradiation. These new hybrids contain a 1,4-disubstituted 1,2,3-triazole ring at the 3-OH posi- tion of quercetin whilst the remaining hydroxyl groups were either pro- tected as methyl or benzyl groups or left unprotected. All the querce- tin-1,2,3-triazole hybrids I–IV were evaluated against REM-134 canine mammary cancer cell line, which is used as a translational model for hu- man breast cancer. These new analogues exhibit potent antiprolifera- tive activity against this cancer cell line. Furthermore, the results show that some of the new quercetin-1,2,3-triazole hybrids have better activ- ity than quercetin. Our best inhibitors displayed IC50 values in the range of 41–180 nM, and undoubtedly will have an important impact on the treatment of both canine and human breast cancer.Thieme2023-02-09T16:20:35Z2023-02-092022-06-08T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://hdl.handle.net/10174/34077http://hdl.handle.net/10174/34077https://doi.org/10.1055/s-0040-1719928porbetepc@uevora.ptacrc@uevora.ptcmma@uevora.pt307Carreiro, ElisabeteCosta, AnaAntunes, Céliainfo: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:RCAAP2024-01-03T19:36:27Zoai:dspace.uevora.pt:10174/34077Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T01:22:47.912445Repositório 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 |
Synthesis and Antiproliferative Activity of Novel Quercetin-1,2,3- Triazole Hybrids using the 1,3-Dipolar Cycloaddition (Click) Reaction |
title |
Synthesis and Antiproliferative Activity of Novel Quercetin-1,2,3- Triazole Hybrids using the 1,3-Dipolar Cycloaddition (Click) Reaction |
spellingShingle |
Synthesis and Antiproliferative Activity of Novel Quercetin-1,2,3- Triazole Hybrids using the 1,3-Dipolar Cycloaddition (Click) Reaction Carreiro, Elisabete 1,2,3-triazole Quercetin Huisgen reaction molecular hybridization anticancer flavonoid |
title_short |
Synthesis and Antiproliferative Activity of Novel Quercetin-1,2,3- Triazole Hybrids using the 1,3-Dipolar Cycloaddition (Click) Reaction |
title_full |
Synthesis and Antiproliferative Activity of Novel Quercetin-1,2,3- Triazole Hybrids using the 1,3-Dipolar Cycloaddition (Click) Reaction |
title_fullStr |
Synthesis and Antiproliferative Activity of Novel Quercetin-1,2,3- Triazole Hybrids using the 1,3-Dipolar Cycloaddition (Click) Reaction |
title_full_unstemmed |
Synthesis and Antiproliferative Activity of Novel Quercetin-1,2,3- Triazole Hybrids using the 1,3-Dipolar Cycloaddition (Click) Reaction |
title_sort |
Synthesis and Antiproliferative Activity of Novel Quercetin-1,2,3- Triazole Hybrids using the 1,3-Dipolar Cycloaddition (Click) Reaction |
author |
Carreiro, Elisabete |
author_facet |
Carreiro, Elisabete Costa, Ana Antunes, Célia |
author_role |
author |
author2 |
Costa, Ana Antunes, Célia |
author2_role |
author author |
dc.contributor.author.fl_str_mv |
Carreiro, Elisabete Costa, Ana Antunes, Célia |
dc.subject.por.fl_str_mv |
1,2,3-triazole Quercetin Huisgen reaction molecular hybridization anticancer flavonoid |
topic |
1,2,3-triazole Quercetin Huisgen reaction molecular hybridization anticancer flavonoid |
description |
Twenty-three new quercetin-1,2,3-triazole hybrids were synthesized in good to quantitative yields via Cu(I)-catalyzed azide- alkyne cycloaddition reaction under microwave irradiation. These new hybrids contain a 1,4-disubstituted 1,2,3-triazole ring at the 3-OH posi- tion of quercetin whilst the remaining hydroxyl groups were either pro- tected as methyl or benzyl groups or left unprotected. All the querce- tin-1,2,3-triazole hybrids I–IV were evaluated against REM-134 canine mammary cancer cell line, which is used as a translational model for hu- man breast cancer. These new analogues exhibit potent antiprolifera- tive activity against this cancer cell line. Furthermore, the results show that some of the new quercetin-1,2,3-triazole hybrids have better activ- ity than quercetin. Our best inhibitors displayed IC50 values in the range of 41–180 nM, and undoubtedly will have an important impact on the treatment of both canine and human breast cancer. |
publishDate |
2022 |
dc.date.none.fl_str_mv |
2022-06-08T00:00:00Z 2023-02-09T16:20:35Z 2023-02-09 |
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/10174/34077 http://hdl.handle.net/10174/34077 https://doi.org/10.1055/s-0040-1719928 |
url |
http://hdl.handle.net/10174/34077 https://doi.org/10.1055/s-0040-1719928 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.none.fl_str_mv |
betepc@uevora.pt acrc@uevora.pt cmma@uevora.pt 307 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.publisher.none.fl_str_mv |
Thieme |
publisher.none.fl_str_mv |
Thieme |
dc.source.none.fl_str_mv |
reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação instacron:RCAAP |
instname_str |
Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
instacron_str |
RCAAP |
institution |
RCAAP |
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 |
repository.mail.fl_str_mv |
|
_version_ |
1799136710130401280 |