Butenafine and analogues: an expeditious synthesis and cytotoxicity and antifungal activities
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2018 |
| Outros Autores: | , , , , , , , , , , , , , |
| Tipo de documento: | Artigo |
| Idioma: | eng |
| Título da fonte: | Repositório Institucional da UFMG |
| Texto Completo: | https://doi.org/10.1016/j.jare.2018.06.004 http://hdl.handle.net/1843/63633 https://orcid.org/0000-0002-9578-7648 https://orcid.org/0000-0002-4032-0100 https://orcid.org/0000-0002-1447-6670 https://orcid.org/0000-0002-4255-3047 https://orcid.org/0000-0002-1108-5666 https://orcid.org/0000-0002-6220-1321 https://orcid.org/0000-0001-5233-1221 https://orcid.org/0000-0002-4624-0777 https://orcid.org/0000-0001-6974-3724 https://orcid.org/0000-0003-2344-5590 |
Resumo: | CNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológico |
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2024-02-01T17:25:48Z2024-02-01T17:25:48Z2018148191https://doi.org/10.1016/j.jare.2018.06.0042090-1232http://hdl.handle.net/1843/63633https://orcid.org/0000-0002-9578-7648https://orcid.org/0000-0002-4032-0100https://orcid.org/0000-0002-1447-6670https://orcid.org/0000-0002-4255-3047https://orcid.org/0000-0002-1108-5666https://orcid.org/0000-0002-6220-1321https://orcid.org/0000-0001-5233-1221https://orcid.org/0000-0002-4624-0777https://orcid.org/0000-0001-6974-3724https://orcid.org/0000-0003-2344-5590CNPq - Conselho Nacional de Desenvolvimento Científico e TecnológicoFAPEMIG - Fundação de Amparo à Pesquisa do Estado de Minas GeraisCAPES - Coordenação de Aperfeiçoamento de Pessoal de Nível SuperiorThe incidence of fungal infections is considered a serious public health problem worldwide. The limited number of antimycotic drugs available to treat human and animal mycosis, the undesirable side effects and toxicities of the currently available drugs, and the emergence of fungal resistance emphasizes the urgent need for more effective antimycotic medicines. In this paper, we describe a rapid, simple, and efficient synthetic route for preparation of the antifungal agent butenafine on a multigram scale. This novel synthetic route also facilitated the preparation of 17 butenafine analogues using Schiff bases as precursors in three steps or less. All the synthesized compounds were evaluated against the yeast, Cryptococcus neoformans/C. gattii species complexes and the filamentous fungi Trichophyton rubrum and Microsporum gypseum. Amine 4bd, a demethylated analogue of butenafine, and its corresponding hydrochloride salt showed low toxicity in vitro and in vivo while maintaining inhibitory activity against filamentous fungi.engUniversidade Federal de Minas GeraisUFMGBrasilICB - DEPARTAMENTO DE MICROBIOLOGIAICX - DEPARTAMENTO DE QUÍMICAJournal of Advanced ResearchQuímicaAtividade antifúngicaAntimicóticoSchiff, Bases deDermatófitosFungos filamentososMicrobiologia - SíntesesAntifungal activityButenafineMicrowave-assisted synthesisMultigram-scale synthesisSchiff baseTrichophyton rubrumButenafine and analogues: an expeditious synthesis and cytotoxicity and antifungal activitiesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttps://www.sciencedirect.com/science/article/pii/S209012321830078XAna María Garzón PorrasBruna Silva TerraTaniris Cafiero BragaThais Furtado Ferreira MagalhãesCleide Viviane Buzanello MartinsDanielle Letícia da SilvaLudmila de Matos BaltazarLudmila Ferreira GouveiaGustavo José Cota de FreitasDaniel de Assis SantosMaria Aparecida de Resende StoianoffBeth Burgwyn FuchsEleftherios MylonakisRossimiriam Pereira de FreitasÂngelo de Fátimaapplication/pdfinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da UFMGinstname:Universidade Federal de Minas Gerais (UFMG)instacron:UFMGLICENSELicense.txtLicense.txttext/plain; charset=utf-82042https://repositorio.ufmg.br/bitstream/1843/63633/1/License.txtfa505098d172de0bc8864fc1287ffe22MD51ORIGINALButenafine and analogues.pdfButenafine and analogues.pdfapplication/pdf959840https://repositorio.ufmg.br/bitstream/1843/63633/2/Butenafine%20and%20analogues.pdf0b594cedf5c419c04839643f08b1f199MD521843/636332024-02-01 14:25:49.093oai:repositorio.ufmg.br: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Repositório de PublicaçõesPUBhttps://repositorio.ufmg.br/oaiopendoar:2024-02-01T17:25:49Repositório Institucional da UFMG - Universidade Federal de Minas Gerais (UFMG)false |
| dc.title.pt_BR.fl_str_mv |
Butenafine and analogues: an expeditious synthesis and cytotoxicity and antifungal activities |
| title |
Butenafine and analogues: an expeditious synthesis and cytotoxicity and antifungal activities |
| spellingShingle |
Butenafine and analogues: an expeditious synthesis and cytotoxicity and antifungal activities Ana María Garzón Porras Antifungal activity Butenafine Microwave-assisted synthesis Multigram-scale synthesis Schiff base Trichophyton rubrum Química Atividade antifúngica Antimicótico Schiff, Bases de Dermatófitos Fungos filamentosos Microbiologia - Sínteses |
| title_short |
Butenafine and analogues: an expeditious synthesis and cytotoxicity and antifungal activities |
| title_full |
Butenafine and analogues: an expeditious synthesis and cytotoxicity and antifungal activities |
| title_fullStr |
Butenafine and analogues: an expeditious synthesis and cytotoxicity and antifungal activities |
| title_full_unstemmed |
Butenafine and analogues: an expeditious synthesis and cytotoxicity and antifungal activities |
| title_sort |
Butenafine and analogues: an expeditious synthesis and cytotoxicity and antifungal activities |
| author |
Ana María Garzón Porras |
| author_facet |
Ana María Garzón Porras Bruna Silva Terra Taniris Cafiero Braga Thais Furtado Ferreira Magalhães Cleide Viviane Buzanello Martins Danielle Letícia da Silva Ludmila de Matos Baltazar Ludmila Ferreira Gouveia Gustavo José Cota de Freitas Daniel de Assis Santos Maria Aparecida de Resende Stoianoff Beth Burgwyn Fuchs Eleftherios Mylonakis Rossimiriam Pereira de Freitas Ângelo de Fátima |
| author_role |
author |
| author2 |
Bruna Silva Terra Taniris Cafiero Braga Thais Furtado Ferreira Magalhães Cleide Viviane Buzanello Martins Danielle Letícia da Silva Ludmila de Matos Baltazar Ludmila Ferreira Gouveia Gustavo José Cota de Freitas Daniel de Assis Santos Maria Aparecida de Resende Stoianoff Beth Burgwyn Fuchs Eleftherios Mylonakis Rossimiriam Pereira de Freitas Ângelo de Fátima |
| author2_role |
author author author author author author author author author author author author author author |
| dc.contributor.author.fl_str_mv |
Ana María Garzón Porras Bruna Silva Terra Taniris Cafiero Braga Thais Furtado Ferreira Magalhães Cleide Viviane Buzanello Martins Danielle Letícia da Silva Ludmila de Matos Baltazar Ludmila Ferreira Gouveia Gustavo José Cota de Freitas Daniel de Assis Santos Maria Aparecida de Resende Stoianoff Beth Burgwyn Fuchs Eleftherios Mylonakis Rossimiriam Pereira de Freitas Ângelo de Fátima |
| dc.subject.por.fl_str_mv |
Antifungal activity Butenafine Microwave-assisted synthesis Multigram-scale synthesis Schiff base Trichophyton rubrum |
| topic |
Antifungal activity Butenafine Microwave-assisted synthesis Multigram-scale synthesis Schiff base Trichophyton rubrum Química Atividade antifúngica Antimicótico Schiff, Bases de Dermatófitos Fungos filamentosos Microbiologia - Sínteses |
| dc.subject.other.pt_BR.fl_str_mv |
Química Atividade antifúngica Antimicótico Schiff, Bases de Dermatófitos Fungos filamentosos Microbiologia - Sínteses |
| description |
CNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológico |
| publishDate |
2018 |
| dc.date.issued.fl_str_mv |
2018 |
| dc.date.accessioned.fl_str_mv |
2024-02-01T17:25:48Z |
| dc.date.available.fl_str_mv |
2024-02-01T17:25:48Z |
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info:eu-repo/semantics/publishedVersion |
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info:eu-repo/semantics/article |
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article |
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publishedVersion |
| dc.identifier.uri.fl_str_mv |
http://hdl.handle.net/1843/63633 |
| dc.identifier.doi.pt_BR.fl_str_mv |
https://doi.org/10.1016/j.jare.2018.06.004 |
| dc.identifier.issn.pt_BR.fl_str_mv |
2090-1232 |
| dc.identifier.orcid.pt_BR.fl_str_mv |
https://orcid.org/0000-0002-9578-7648 https://orcid.org/0000-0002-4032-0100 https://orcid.org/0000-0002-1447-6670 https://orcid.org/0000-0002-4255-3047 https://orcid.org/0000-0002-1108-5666 https://orcid.org/0000-0002-6220-1321 https://orcid.org/0000-0001-5233-1221 https://orcid.org/0000-0002-4624-0777 https://orcid.org/0000-0001-6974-3724 https://orcid.org/0000-0003-2344-5590 |
| url |
https://doi.org/10.1016/j.jare.2018.06.004 http://hdl.handle.net/1843/63633 https://orcid.org/0000-0002-9578-7648 https://orcid.org/0000-0002-4032-0100 https://orcid.org/0000-0002-1447-6670 https://orcid.org/0000-0002-4255-3047 https://orcid.org/0000-0002-1108-5666 https://orcid.org/0000-0002-6220-1321 https://orcid.org/0000-0001-5233-1221 https://orcid.org/0000-0002-4624-0777 https://orcid.org/0000-0001-6974-3724 https://orcid.org/0000-0003-2344-5590 |
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2090-1232 |
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eng |
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eng |
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Journal of Advanced Research |
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info:eu-repo/semantics/openAccess |
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openAccess |
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application/pdf |
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Universidade Federal de Minas Gerais |
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UFMG |
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Brasil |
| dc.publisher.department.fl_str_mv |
ICB - DEPARTAMENTO DE MICROBIOLOGIA ICX - DEPARTAMENTO DE QUÍMICA |
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Universidade Federal de Minas Gerais |
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reponame:Repositório Institucional da UFMG instname:Universidade Federal de Minas Gerais (UFMG) instacron:UFMG |
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