OBJECTIVES:

To synthesize and evaluate the antifungal action of prop-2-yn-1-yl 4,6-di-O-acetyl-2,3- dideoxy-α-D-erythro-hex-2-enopyranoside against non-albicans species of Candida as well as to evaluate its antimicrobial activity when associated with amphotericin B or with ketoconazole.

MATERIALS AND METHODS:

The synthesis of this glycoside was obtained by the glycosylation reaction using tri-O-acetyl-D-glucal, 2-propyn-1-ol alcohol and montmorillonite K-10. The antifungal activity test was performed by the broth microdilution method and the association with amphotericin B or ketoconazole by the checkerboard method.

RESULTS:

The glycoside was obtained with 95% yield after the reaction time of 1 h and did not present antifungal activity at the tested concentrations (512; 0.5 μg/mL) when tested alone. When combined with amphotericin B (minimum inhibitory concentration - MIC 2 μg/mL) or ketoconazole (MIC 0.5 μg/mL), synergism and indifference were observed respectively.

CONCLUSION:

Glycoside 3 was obtained in excellent yield and did not present antifungal activity against the strains of non-albicans species. But, when associated with amphotericin B, the activity was promising; with ketoconazole, indifferent.