Inibição do crescimento de microrganismos patogênicos induzida por butenolídeos análogos aos cadiolídeos
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Universidade Federal de Minas Gerais
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Artigo de periódico
Título alternativo
Inhibitory effect on growth of pathogenic microorganisms induced by butenolides related to cadiolides
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Membros da banca
Resumo
The increasing number of antibiotic resistant microorganisms requires the development of new drugs. In this context, natural cadiolides are promising leads as they present potent antimicrobial activity and low cytotoxicity. In this work we report the synthesis of 21 new cadiolide analogues. The synthesis involved a Diels−Alder cycloaddition/ cycloreversion reaction between an oxazole and different ynones, affording four intermediate butenolides (14a-d) in 61-81% yield. These intermediates were subjected to a vinylogous Knoevenagel condensation, followed by demethylation of the methoxylated compounds, affording all 21 analogues in good yields. The antibiotic activity of all compounds was evaluated against a panel of five microorganisms. The bioassays on the microbial growth showed that the cadiolides are more active for Gram-positive than Gram-negative bacteria, and have low activity against the fungus C. albicans. The most active compounds (14b, 15b, 15c and 16e) were effective against S. aureus showing IC50 in the range of 1.8-6.0 µg mL-1. The results also indicated that the nature and position of substituent groups on the aromatic moieties have some effect on the activities.
Abstract
Assunto
Microorganismos patogênicos, Química
Palavras-chave
Cadiolides, Butenolides, Growth inhibition, Pathogenic microorganisms
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Endereço externo
https://www.scielo.br/j/qn/a/gmRPdDLwzs6C7gRhNh4hGHL/