Butenafine and analogues: An expeditious synthesis and cytotoxicity and antifungal activities
The 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 emphas...
| Main Authors: | , , , , , , , , , , , , , , |
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| Format: | Article |
| Language: | English |
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Elsevier
2018-11-01
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| Series: | Journal of Advanced Research |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S209012321830078X |
| _version_ | 1819209019492925440 |
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| author | Ana María Garzón Porras Bruna Silva Terra Taniris Cafiero Braga Thais Furtado Ferreira Magalhães Cleide Viviane Buzanello Martins Danielle Letícia da Silva Ludmila Matos Baltazar Ludmila Ferreira Gouveia Gustavo José Cota de Freitas Daniel Assis Santos Maria Aparecida Resende-Stoianoff Beth Burgwyn Fuchs Eleftherios Mylonakis Rossimiriam Pereira de Freitas Ângelo de Fátima |
| 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 Matos Baltazar Ludmila Ferreira Gouveia Gustavo José Cota de Freitas Daniel Assis Santos Maria Aparecida Resende-Stoianoff Beth Burgwyn Fuchs Eleftherios Mylonakis Rossimiriam Pereira de Freitas Ângelo de Fátima |
| author_sort | Ana María Garzón Porras |
| collection | DOAJ |
| description | The 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. Keywords: Antifungal activity, Butenafine, Microwave-assisted synthesis, Multigram-scale synthesis, Schiff base, Trichophyton rubrum |
| first_indexed | 2024-12-23T05:48:38Z |
| format | Article |
| id | doaj.art-dd1efab29fca452e922562490979816e |
| institution | Directory Open Access Journal |
| issn | 2090-1232 |
| language | English |
| last_indexed | 2024-12-23T05:48:38Z |
| publishDate | 2018-11-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Journal of Advanced Research |
| spelling | doaj.art-dd1efab29fca452e922562490979816e2022-12-21T17:58:02ZengElsevierJournal of Advanced Research2090-12322018-11-01148191Butenafine and analogues: An expeditious synthesis and cytotoxicity and antifungal activitiesAna María Garzón Porras0Bruna Silva Terra1Taniris Cafiero Braga2Thais Furtado Ferreira Magalhães3Cleide Viviane Buzanello Martins4Danielle Letícia da Silva5Ludmila Matos Baltazar6Ludmila Ferreira Gouveia7Gustavo José Cota de Freitas8Daniel Assis Santos9Maria Aparecida Resende-Stoianoff10Beth Burgwyn Fuchs11Eleftherios Mylonakis12Rossimiriam Pereira de Freitas13Ângelo de Fátima14Departamento de Química, Universidade Federal de Minas Gerais, Belo Horizonte, MG, BrazilDepartamento de Química, Universidade Federal de Minas Gerais, Belo Horizonte, MG, BrazilDepartamento de Química, Universidade Federal de Minas Gerais, Belo Horizonte, MG, BrazilDepartamento de Microbiologia, Universidade Federal de Minas Gerais, Belo Horizonte, MG, Brazil; Division of Infectious Diseases, Rhode Island Hospital, Alpert Medical School of Brown University, Providence, RI, USADivision of Infectious Diseases, Rhode Island Hospital, Alpert Medical School of Brown University, Providence, RI, USA; Centro de Engenharias e Ciências Exatas, Universidade Estadual do Oeste do Paraná, Toledo, PR, BrazilDepartamento de Microbiologia, Universidade Federal de Minas Gerais, Belo Horizonte, MG, Brazil; Division of Infectious Diseases, Rhode Island Hospital, Alpert Medical School of Brown University, Providence, RI, USADepartamento de Microbiologia, Universidade Federal de Minas Gerais, Belo Horizonte, MG, BrazilDepartamento de Microbiologia, Universidade Federal de Minas Gerais, Belo Horizonte, MG, BrazilDepartamento de Microbiologia, Universidade Federal de Minas Gerais, Belo Horizonte, MG, BrazilDepartamento de Microbiologia, Universidade Federal de Minas Gerais, Belo Horizonte, MG, BrazilDepartamento de Microbiologia, Universidade Federal de Minas Gerais, Belo Horizonte, MG, BrazilDivision of Infectious Diseases, Rhode Island Hospital, Alpert Medical School of Brown University, Providence, RI, USADivision of Infectious Diseases, Rhode Island Hospital, Alpert Medical School of Brown University, Providence, RI, USADepartamento de Química, Universidade Federal de Minas Gerais, Belo Horizonte, MG, BrazilDepartamento de Química, Universidade Federal de Minas Gerais, Belo Horizonte, MG, Brazil; Corresponding author.The 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. Keywords: Antifungal activity, Butenafine, Microwave-assisted synthesis, Multigram-scale synthesis, Schiff base, Trichophyton rubrumhttp://www.sciencedirect.com/science/article/pii/S209012321830078X |
| spellingShingle | Ana María Garzón Porras Bruna Silva Terra Taniris Cafiero Braga Thais Furtado Ferreira Magalhães Cleide Viviane Buzanello Martins Danielle Letícia da Silva Ludmila Matos Baltazar Ludmila Ferreira Gouveia Gustavo José Cota de Freitas Daniel Assis Santos Maria Aparecida Resende-Stoianoff Beth Burgwyn Fuchs Eleftherios Mylonakis Rossimiriam Pereira de Freitas Ângelo de Fátima Butenafine and analogues: An expeditious synthesis and cytotoxicity and antifungal activities Journal of Advanced Research |
| title | 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_short | Butenafine and analogues: An expeditious synthesis and cytotoxicity and antifungal activities |
| title_sort | butenafine and analogues an expeditious synthesis and cytotoxicity and antifungal activities |
| url | http://www.sciencedirect.com/science/article/pii/S209012321830078X |
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