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Butenafine and analogues: An expeditious synthesis and cytotoxicity and antifungal activities. 2018
Ana María Garzón Porras, and
Bruna Silva Terra, and
Taniris Cafiero Braga, and
Thais Furtado Ferreira Magalhães, and
Cleide Viviane Buzanello Martins, and
Danielle Letícia da Silva, and
Ludmila Matos Baltazar, and
Ludmila Ferreira Gouveia, and
Gustavo José Cota de Freitas, and
Daniel Assis Santos, and
Maria Aparecida Resende-Stoianoff, and
Beth Burgwyn Fuchs, and
Eleftherios Mylonakis, and
Rossimiriam Pereira de Freitas, and
Ângelo de Fátima
Departamento de Química, Universidade Federal de Minas Gerais, Belo Horizonte, MG, Brazil.
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.
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