Multicomponent and 1,3-dipolar cycloaddition synthesis of triazole- and isoxazole-acridinedione/xanthenedione heterocyclic hybrids: cytotoxic effects on human cancer cells
Autor(a) principal: | |
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Data de Publicação: | 2020 |
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/10773/37402 |
Resumo: | A new series of diverse 1,2,3-triazole-acridinedione/xanthenedione and 1,2-isoxazole-acridinedione/xanthenedione heterocyclic hybrids have been synthesized via 1,3-dipolar coupling reaction of N/O-substituted-acridinedione-alkyne or O-substituted-xanthenedione-alkyne substrates with various aromatic azides or oximes. In all cases, the cycloaddition is totally regioselective. The chemical structures of the synthesized compounds are determined using 2D NMR and are further confirmed by single-crystal X-ray diffraction analysis. Preliminary in vitro cytotoxic assays on two human breast cancer cell lines (MDA-MB-231, T47-D) and one prostate cancer cell line (PC3) are performed on some selected compounds. The most active O-1,2,3-triazole-xanthenedione hybrid displays the best cytotoxicity effects with IC50 ≤ 20 μM in breast cancer and IC50 = 10 μM in prostate cancer cell lines. |
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7160 |
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Multicomponent and 1,3-dipolar cycloaddition synthesis of triazole- and isoxazole-acridinedione/xanthenedione heterocyclic hybrids: cytotoxic effects on human cancer cellsClick chemistryTriazoleIsoxazoleAcridinedioneXanthenedioneAnticancerA new series of diverse 1,2,3-triazole-acridinedione/xanthenedione and 1,2-isoxazole-acridinedione/xanthenedione heterocyclic hybrids have been synthesized via 1,3-dipolar coupling reaction of N/O-substituted-acridinedione-alkyne or O-substituted-xanthenedione-alkyne substrates with various aromatic azides or oximes. In all cases, the cycloaddition is totally regioselective. The chemical structures of the synthesized compounds are determined using 2D NMR and are further confirmed by single-crystal X-ray diffraction analysis. Preliminary in vitro cytotoxic assays on two human breast cancer cell lines (MDA-MB-231, T47-D) and one prostate cancer cell line (PC3) are performed on some selected compounds. The most active O-1,2,3-triazole-xanthenedione hybrid displays the best cytotoxicity effects with IC50 ≤ 20 μM in breast cancer and IC50 = 10 μM in prostate cancer cell lines.Elsevier2023-04-27T11:07:09Z2020-10-05T00:00:00Z2020-10-05info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10773/37402eng0022-286010.1016/j.molstruc.2020.128325Naouri, AbdelkaderDjemoui, AmarOuahrani, Mouhamad RidhaLahrech, Mokhtar BoualemLemouari, NajetRocha, Djenisa H.A.Albuquerque, HélioMendes, Ricardo F.Almeida Paz, Filipe A.Helguero, Luisa A.Bachari, KhaldounTalhi, OualidSilva, Artur M.S.info: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:RCAAP2024-02-22T12:12:11Zoai:ria.ua.pt:10773/37402Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T03:08:00.531769Repositório 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 |
Multicomponent and 1,3-dipolar cycloaddition synthesis of triazole- and isoxazole-acridinedione/xanthenedione heterocyclic hybrids: cytotoxic effects on human cancer cells |
title |
Multicomponent and 1,3-dipolar cycloaddition synthesis of triazole- and isoxazole-acridinedione/xanthenedione heterocyclic hybrids: cytotoxic effects on human cancer cells |
spellingShingle |
Multicomponent and 1,3-dipolar cycloaddition synthesis of triazole- and isoxazole-acridinedione/xanthenedione heterocyclic hybrids: cytotoxic effects on human cancer cells Naouri, Abdelkader Click chemistry Triazole Isoxazole Acridinedione Xanthenedione Anticancer |
title_short |
Multicomponent and 1,3-dipolar cycloaddition synthesis of triazole- and isoxazole-acridinedione/xanthenedione heterocyclic hybrids: cytotoxic effects on human cancer cells |
title_full |
Multicomponent and 1,3-dipolar cycloaddition synthesis of triazole- and isoxazole-acridinedione/xanthenedione heterocyclic hybrids: cytotoxic effects on human cancer cells |
title_fullStr |
Multicomponent and 1,3-dipolar cycloaddition synthesis of triazole- and isoxazole-acridinedione/xanthenedione heterocyclic hybrids: cytotoxic effects on human cancer cells |
title_full_unstemmed |
Multicomponent and 1,3-dipolar cycloaddition synthesis of triazole- and isoxazole-acridinedione/xanthenedione heterocyclic hybrids: cytotoxic effects on human cancer cells |
title_sort |
Multicomponent and 1,3-dipolar cycloaddition synthesis of triazole- and isoxazole-acridinedione/xanthenedione heterocyclic hybrids: cytotoxic effects on human cancer cells |
author |
Naouri, Abdelkader |
author_facet |
Naouri, Abdelkader Djemoui, Amar Ouahrani, Mouhamad Ridha Lahrech, Mokhtar Boualem Lemouari, Najet Rocha, Djenisa H.A. Albuquerque, Hélio Mendes, Ricardo F. Almeida Paz, Filipe A. Helguero, Luisa A. Bachari, Khaldoun Talhi, Oualid Silva, Artur M.S. |
author_role |
author |
author2 |
Djemoui, Amar Ouahrani, Mouhamad Ridha Lahrech, Mokhtar Boualem Lemouari, Najet Rocha, Djenisa H.A. Albuquerque, Hélio Mendes, Ricardo F. Almeida Paz, Filipe A. Helguero, Luisa A. Bachari, Khaldoun Talhi, Oualid Silva, Artur M.S. |
author2_role |
author author author author author author author author author author author author |
dc.contributor.author.fl_str_mv |
Naouri, Abdelkader Djemoui, Amar Ouahrani, Mouhamad Ridha Lahrech, Mokhtar Boualem Lemouari, Najet Rocha, Djenisa H.A. Albuquerque, Hélio Mendes, Ricardo F. Almeida Paz, Filipe A. Helguero, Luisa A. Bachari, Khaldoun Talhi, Oualid Silva, Artur M.S. |
dc.subject.por.fl_str_mv |
Click chemistry Triazole Isoxazole Acridinedione Xanthenedione Anticancer |
topic |
Click chemistry Triazole Isoxazole Acridinedione Xanthenedione Anticancer |
description |
A new series of diverse 1,2,3-triazole-acridinedione/xanthenedione and 1,2-isoxazole-acridinedione/xanthenedione heterocyclic hybrids have been synthesized via 1,3-dipolar coupling reaction of N/O-substituted-acridinedione-alkyne or O-substituted-xanthenedione-alkyne substrates with various aromatic azides or oximes. In all cases, the cycloaddition is totally regioselective. The chemical structures of the synthesized compounds are determined using 2D NMR and are further confirmed by single-crystal X-ray diffraction analysis. Preliminary in vitro cytotoxic assays on two human breast cancer cell lines (MDA-MB-231, T47-D) and one prostate cancer cell line (PC3) are performed on some selected compounds. The most active O-1,2,3-triazole-xanthenedione hybrid displays the best cytotoxicity effects with IC50 ≤ 20 μM in breast cancer and IC50 = 10 μM in prostate cancer cell lines. |
publishDate |
2020 |
dc.date.none.fl_str_mv |
2020-10-05T00:00:00Z 2020-10-05 2023-04-27T11:07:09Z |
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/10773/37402 |
url |
http://hdl.handle.net/10773/37402 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
0022-2860 10.1016/j.molstruc.2020.128325 |
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.publisher.none.fl_str_mv |
Elsevier |
publisher.none.fl_str_mv |
Elsevier |
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 |
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1799137733891850240 |