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Pure Appl. Chem. Vol. 73, No. 9, pp. 1475-1485 (2001)

Pure and Applied Chemistry

Vol. 73, Issue 9


Rational design and synthesis of homochiral azole antifungal agents*

Maurizio Botta, Federico Corelli, Fabrizio Manetti, Claudia Mugnaini, and Andrea Tafi

Dipartimento Farmaco Chimico Tecnologico, Università degli Studi di Siena, Via A. Moro, 53100 Siena, Italy

Abstract: 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.

*Plenary lecture presented at the Hungarian-German-Italian-Polish Joint Meeting on Medicinal Chemistry, Budapest, Hungary, 2 –6 September 2001. Other presentations are published in this issue, pp. 1387-1509.

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