Azole antifungal agents related to naftifine and butenafine

The methyl group of naftifine (1) and butenafine (2) was replaced by an azo lic nucleus to obtain the new compounds 3-8 which exhibit the characteristi cs of both allylamine (or benzylamine) and azole antifungals. The title com pounds were evaluated in vitro against several pathogenic fungi responsible for human disease. Among these, compounds 5, 6, and 8 were found to inhibi t the growth of dermatophytes with a potency comparable to that of naftifin e. The synthetic sequence includes the preparation of aminoazole Schiff bas es, reduction, and alkylation of the corresponding secondary amines.