Improved microwave-mediated synthesis of 3-(3-aryl-1,2,4-oxadiazol-5-yl)propionic acids and their larvicidal and fungal growth inhibitory properties
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2009 |
| Outros Autores: | , , , , , , , , |
| Tipo de documento: | Artigo |
| Idioma: | eng |
| Título da fonte: | Repositório Institucional da FIOCRUZ (ARCA) |
| Texto Completo: | https://www.arca.fiocruz.br/handle/icict/27831 |
Resumo: | CNPq, Centro de Pesquisas Científicas e Pesquisas do Estado de Pernambuco e Fundação (FACEPE, PRONEX 200-CNPq) |
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Neves Filho, Ricardo Antonio WanderleySilva, Cecília Aguiar daSilva, Clécia Sipriano Borges daBrustein, Vanessa PassosNavarro, Daniela Maria do Amaral FerrazSantos, Fábio André Brayner dosAlves, Luiz CarlosCavalcanti, Marília Gabriela dos SantosSrivastava, Rajendra MohanCarneiro-Da-Cunha, Maria das Graças2018-08-03T13:20:19Z2018-08-03T13:20:19Z2009NEVES FILHO, Ricardo Antonio Wanderley et al. Improved Microwave-Mediated Synthesis of 3-(3-Aryl-1,2,4-Oxadiazol-5-Yl)Propionic Acids and Their Larvicidal and Fungal Growth Inhibitory Properties. Chemical & Pharmaceutical Bulletin, v. 57, n. 8, p. 819–825, ago. 2009.0009-2363https://www.arca.fiocruz.br/handle/icict/2783110.1248/cpb.57.819CNPq, Centro de Pesquisas Científicas e Pesquisas do Estado de Pernambuco e Fundação (FACEPE, PRONEX 200-CNPq)Universidade Federal de Pernambuco. Departamento de Química Fundamental. Recife, PE, Brazil.Universidade Federal de Pernambuco. Departamento de Química Fundamental. Recife, PE, Brazil.Universidade Federal de Pernambuco. Departamento de Química Fundamental. Recife, PE, Brazil.Universidade Federal de Pernambuco. Departamento de Bioquímica. Recife, PE, Brazil.Universidade Federal de Pernambuco. Departamento de Química Fundamental. Recife, PE, Brazil.Fundação Oswaldo Cruz. Instituto Aggeu Magalhães. Departamento de Parasitologia. Recife, PE, Brasil / Universidade Federal de Pernambuco. Laboratório de Imunopatologia. Recife, PE, Brasil.Fundação Oswaldo Cruz. Instituto Aggeu Magalhães. Departamento de Parasitologia. Recife, PE, Brasil / Universidade Federal de Pernambuco. Laboratório de Imunopatologia. Recife, PE, Brasil.Fundação Oswaldo Cruz. Instituto Aggeu Magalhães. Departamento de Parasitologia. Recife, PE, Brasil / Universidade Federal de Pernambuco. Laboratório de Imunopatologia. Recife, PE, Brasil.Universidade Federal de Pernambuco. Departamento de Química Fundamental. Recife, PE, Brazil.Universidade Federal de Pernambuco. Departamento de Bioquímica. Recife, PE, Brazil.The synthesis of 3-(3-aryl-1,2,4-oxadiazol-5-yl)propionic acids from arylamidoximes and succinic anhydride under focused microwave irradiation conditions is described. The new synthetic method furnished the desired products in 2-3 min and good yields. Furthermore, the previously complicated purification procedure has been simplified in a manner which is quick, eco-friendly and cost-effective. Larvicidal bioassay and fungal growth inhibitory tests were performed using several 3-(3-aryl-1,2,4-oxadiazol-5-yl)propionic acids. These acids presented strong larvicidal activity against L4 larvae of Aedes aegypti. The results suggest that larvicidal activity might be correlated with the presence of electron-withdrawing substituents in the para position of the phenyl ring except the fluorine atom. The alterations observed in the larvae spiracular valves of the siphon and anal papillae by 1,2,4-oxadiazoles in the larvicidal bioassay are responsible for larvae's death. Furthermore, all acids inhibited the fungal growth of five different types of fungi, viz., Fusarium solani, F. oxysporum, F. moniliforme, F. decemcellulare and F. lateritium in a preliminary evaluation. Both of these activities are being disclosed for the first time for 1,2,4-oxadiazole-5-yl ring linked at C-3 of propionic acid.eng1,2,4-oxadiazoleÁcido propiônicoLarvicidaAedes aegyptiAtividade antifúngica1,2,4-oxadiazolePropionic acidLarvicideAedes aegyptiAntifungal activityAedes / efeitos de drogasAnimaisAntifúngicos / síntese químicaAgentes antifúngicos / químicaAntifúngicos / farmacologiaFusarium / efeitos de drogasFusarium / crescimento & desenvolvimentoInseticidas / síntese químicaInseticidas / QuímicaInseticidas / farmacologiaLarva / efeitos de drogasTestes de Sensibilidade MicrobianaMicroondasEstrutura molecularOxadiazóis / síntese químicaOxadiazoles / químicaOxadiazoles / farmacologiaPropionatos / síntese químicaPropionatos / químicaPropionatos / farmacologiaEstereoisomerismoRelação Estrutura-AtividadeImproved microwave-mediated synthesis of 3-(3-aryl-1,2,4-oxadiazol-5-yl)propionic acids and their larvicidal and fungal growth inhibitory propertiesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da FIOCRUZ (ARCA)instname:Fundação Oswaldo Cruz (FIOCRUZ)instacron:FIOCRUZLICENSElicense.txtlicense.txttext/plain; charset=utf-83092https://www.arca.fiocruz.br/bitstream/icict/27831/1/license.txt447f2497af1ef5cf99b5c07f6fa18dceMD51ORIGINALImproved Microwave-Mediated Synthesis of 3-(3-Aryl-1,2,4-oxadiazol-5-.pdfImproved Microwave-Mediated Synthesis of 3-(3-Aryl-1,2,4-oxadiazol-5-.pdfapplication/pdf1010714https://www.arca.fiocruz.br/bitstream/icict/27831/2/Improved%20Microwave-Mediated%20Synthesis%20of%203-%283-Aryl-1%2c2%2c4-oxadiazol-5-.pdff133f76c6eb9139c04c7ae52032a14ebMD52icict/278312018-08-03 22:13:00.33oai:www.arca.fiocruz.br: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Repositório InstitucionalPUBhttps://www.arca.fiocruz.br/oai/requestrepositorio.arca@fiocruz.bropendoar:21352018-08-04T01:13Repositório Institucional da FIOCRUZ (ARCA) - Fundação Oswaldo Cruz (FIOCRUZ)false |
| dc.title.pt_BR.fl_str_mv |
Improved microwave-mediated synthesis of 3-(3-aryl-1,2,4-oxadiazol-5-yl)propionic acids and their larvicidal and fungal growth inhibitory properties |
| title |
Improved microwave-mediated synthesis of 3-(3-aryl-1,2,4-oxadiazol-5-yl)propionic acids and their larvicidal and fungal growth inhibitory properties |
| spellingShingle |
Improved microwave-mediated synthesis of 3-(3-aryl-1,2,4-oxadiazol-5-yl)propionic acids and their larvicidal and fungal growth inhibitory properties Neves Filho, Ricardo Antonio Wanderley 1,2,4-oxadiazole Ácido propiônico Larvicida Aedes aegypti Atividade antifúngica 1,2,4-oxadiazole Propionic acid Larvicide Aedes aegypti Antifungal activity Aedes / efeitos de drogas Animais Antifúngicos / síntese química Agentes antifúngicos / química Antifúngicos / farmacologia Fusarium / efeitos de drogas Fusarium / crescimento & desenvolvimento Inseticidas / síntese química Inseticidas / Química Inseticidas / farmacologia Larva / efeitos de drogas Testes de Sensibilidade Microbiana Microondas Estrutura molecular Oxadiazóis / síntese química Oxadiazoles / química Oxadiazoles / farmacologia Propionatos / síntese química Propionatos / química Propionatos / farmacologia Estereoisomerismo Relação Estrutura-Atividade |
| title_short |
Improved microwave-mediated synthesis of 3-(3-aryl-1,2,4-oxadiazol-5-yl)propionic acids and their larvicidal and fungal growth inhibitory properties |
| title_full |
Improved microwave-mediated synthesis of 3-(3-aryl-1,2,4-oxadiazol-5-yl)propionic acids and their larvicidal and fungal growth inhibitory properties |
| title_fullStr |
Improved microwave-mediated synthesis of 3-(3-aryl-1,2,4-oxadiazol-5-yl)propionic acids and their larvicidal and fungal growth inhibitory properties |
| title_full_unstemmed |
Improved microwave-mediated synthesis of 3-(3-aryl-1,2,4-oxadiazol-5-yl)propionic acids and their larvicidal and fungal growth inhibitory properties |
| title_sort |
Improved microwave-mediated synthesis of 3-(3-aryl-1,2,4-oxadiazol-5-yl)propionic acids and their larvicidal and fungal growth inhibitory properties |
| author |
Neves Filho, Ricardo Antonio Wanderley |
| author_facet |
Neves Filho, Ricardo Antonio Wanderley Silva, Cecília Aguiar da Silva, Clécia Sipriano Borges da Brustein, Vanessa Passos Navarro, Daniela Maria do Amaral Ferraz Santos, Fábio André Brayner dos Alves, Luiz Carlos Cavalcanti, Marília Gabriela dos Santos Srivastava, Rajendra Mohan Carneiro-Da-Cunha, Maria das Graças |
| author_role |
author |
| author2 |
Silva, Cecília Aguiar da Silva, Clécia Sipriano Borges da Brustein, Vanessa Passos Navarro, Daniela Maria do Amaral Ferraz Santos, Fábio André Brayner dos Alves, Luiz Carlos Cavalcanti, Marília Gabriela dos Santos Srivastava, Rajendra Mohan Carneiro-Da-Cunha, Maria das Graças |
| author2_role |
author author author author author author author author author |
| dc.contributor.author.fl_str_mv |
Neves Filho, Ricardo Antonio Wanderley Silva, Cecília Aguiar da Silva, Clécia Sipriano Borges da Brustein, Vanessa Passos Navarro, Daniela Maria do Amaral Ferraz Santos, Fábio André Brayner dos Alves, Luiz Carlos Cavalcanti, Marília Gabriela dos Santos Srivastava, Rajendra Mohan Carneiro-Da-Cunha, Maria das Graças |
| dc.subject.other.pt_BR.fl_str_mv |
1,2,4-oxadiazole Ácido propiônico Larvicida Aedes aegypti Atividade antifúngica |
| topic |
1,2,4-oxadiazole Ácido propiônico Larvicida Aedes aegypti Atividade antifúngica 1,2,4-oxadiazole Propionic acid Larvicide Aedes aegypti Antifungal activity Aedes / efeitos de drogas Animais Antifúngicos / síntese química Agentes antifúngicos / química Antifúngicos / farmacologia Fusarium / efeitos de drogas Fusarium / crescimento & desenvolvimento Inseticidas / síntese química Inseticidas / Química Inseticidas / farmacologia Larva / efeitos de drogas Testes de Sensibilidade Microbiana Microondas Estrutura molecular Oxadiazóis / síntese química Oxadiazoles / química Oxadiazoles / farmacologia Propionatos / síntese química Propionatos / química Propionatos / farmacologia Estereoisomerismo Relação Estrutura-Atividade |
| dc.subject.en.pt_BR.fl_str_mv |
1,2,4-oxadiazole Propionic acid Larvicide Aedes aegypti Antifungal activity |
| dc.subject.decs.pt_BR.fl_str_mv |
Aedes / efeitos de drogas Animais Antifúngicos / síntese química Agentes antifúngicos / química Antifúngicos / farmacologia Fusarium / efeitos de drogas Fusarium / crescimento & desenvolvimento Inseticidas / síntese química Inseticidas / Química Inseticidas / farmacologia Larva / efeitos de drogas Testes de Sensibilidade Microbiana Microondas Estrutura molecular Oxadiazóis / síntese química Oxadiazoles / química Oxadiazoles / farmacologia Propionatos / síntese química Propionatos / química Propionatos / farmacologia Estereoisomerismo Relação Estrutura-Atividade |
| description |
CNPq, Centro de Pesquisas Científicas e Pesquisas do Estado de Pernambuco e Fundação (FACEPE, PRONEX 200-CNPq) |
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2009 |
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2009 |
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2018-08-03T13:20:19Z |
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2018-08-03T13:20:19Z |
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info:eu-repo/semantics/publishedVersion |
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info:eu-repo/semantics/article |
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publishedVersion |
| dc.identifier.citation.fl_str_mv |
NEVES FILHO, Ricardo Antonio Wanderley et al. Improved Microwave-Mediated Synthesis of 3-(3-Aryl-1,2,4-Oxadiazol-5-Yl)Propionic Acids and Their Larvicidal and Fungal Growth Inhibitory Properties. Chemical & Pharmaceutical Bulletin, v. 57, n. 8, p. 819–825, ago. 2009. |
| dc.identifier.uri.fl_str_mv |
https://www.arca.fiocruz.br/handle/icict/27831 |
| dc.identifier.issn.pt_BR.fl_str_mv |
0009-2363 |
| dc.identifier.doi.none.fl_str_mv |
10.1248/cpb.57.819 |
| identifier_str_mv |
NEVES FILHO, Ricardo Antonio Wanderley et al. Improved Microwave-Mediated Synthesis of 3-(3-Aryl-1,2,4-Oxadiazol-5-Yl)Propionic Acids and Their Larvicidal and Fungal Growth Inhibitory Properties. Chemical & Pharmaceutical Bulletin, v. 57, n. 8, p. 819–825, ago. 2009. 0009-2363 10.1248/cpb.57.819 |
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https://www.arca.fiocruz.br/handle/icict/27831 |
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eng |
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eng |
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