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Bioorg Med Chem Lett ; 19(6): 1793-6, 2009 Mar 15.
Artigo em Inglês | MEDLINE | ID: mdl-19232493

RESUMO

The antifungal activity of a complete series of 15 n-alkyl gallates and six analogues acting against a representative panel of opportunistic pathogenic fungi was studied in order to analyze their role in: the importance of the fungi tested, the importance of the hydroxyls, the influence of the chain length and the hydrophobicity of the compounds. It was demonstrated that dermatophytes were the most susceptible species and that hydroxyls appear to be necessary but not sufficient for the activity. When the logP of each gallate was calculated and related to the different values of MIC against Microsporum gypseum it was observed that hexyl, heptyl, octyl and nonyl gallates exhibit a significant positive deviation from the curve corresponding to a polynomial equation obtained for the other gallates. This suggests that these compounds have a further mode of action besides their hydrophobicity, possibly the inhibition of some enzyme involved in ergosterol biosynthesis.


Assuntos
Antifúngicos/síntese química , Antifúngicos/farmacologia , Química Farmacêutica/métodos , Fungos/efeitos dos fármacos , Ácido Gálico/análogos & derivados , Arthrodermataceae/metabolismo , Desenho de Fármacos , Avaliação Pré-Clínica de Medicamentos , Ergosterol/química , Ácido Gálico/química , Testes de Sensibilidade Microbiana , Microsporum/metabolismo , Estrutura Molecular , Relação Estrutura-Atividade
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