Antifungal activity of novel 5-carbonyl derivatives of 3-phenyl-3-(1H-imidazol-1-ylmethyl)-2-methylisoxazolidines.

The synthesis and antifungal activity of a series of novel 5-carbonyl derivatives of 3-phenyl-3-(1H-imidazol-1-ylmethyl)-2-methylisoxazolidines (4) are discussed. The preparation of the title compounds involved a 1,3-dipolar cycloaddition reaction of alpha-substituted ketonitrones with either acrylic esters, acrylamide or methyl vinyl ketone to furnish cis/trans-diastereomeric mixtures of the desired 5-carbonyl isoxazolidines 4. The anifungal activity was evaluated in vitro in solid agar cultures. Some of the compounds tested exerted moderate to potent activity against a wide variety of dermatophytes and yeast and systemic fungi.