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The first synthesis of both enantiomers of the antifungal drug bifonazole (1a) and related imidazole compounds 1i and 5b,c is described, starting from enantiomerically pure or enriched amines 6a­d. Construction of the imidazole ring on amines 6a­d was performed in a straightforward manner affording the final compounds in good overall yield and with very high enantiomeric purity, as determined by enantioselective HPLC. Biological evaluation in vitro of the single enantiomers of 1a,i and 5b,c against different strains of Candida albicans did not show any enantioselectivity. Finally, the pseudoreceptor modeling technique was applied to generate a model able to explain and predict the inhibitory activity of azole compounds against C. albicans P45014DM.

Rational design and synthesis of homochiral azole antifungal agents