Azole antifungal agents related to naftifine and butenafine.
The methyl group of naftifine (1) and butenafine (2) was replaced by an azolic nucleus to obtain the new compounds 3-8 which exhibit the characteristics of both allylamine (or benzylamine) and azole antifungals. The title compounds were evaluated in vitro against several pathogenic fungi responsible for human disease. Among these, compounds 5, 6, and 8 were found to inhibit the growth of dermatophytes with a potency comparable to that of naftifine. The synthetic sequence includes the preparation of aminoazole Schiff bases, reduction, and alkylation of the corresponding secondary amines.
Castellano
S
S
Dipartimento di Scienze Farmaceutiche, Università di Trieste, Trieste, Italy.
La Colla
P
P
Musiu
C
C
Stefancich
G
G
D000499:Allylamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001596:Benzylamines / Q000138:chemical synthesis* / Q000494:pharmacology; D002460:Cell Line; D005658:Fungi / Q000187:drug effects; D006801:Humans; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000494:pharmacology; D013329:Structure-Activity Relationship
D000935:Antifungal Agents; D001596:Benzylamines; D009281:Naphthalenes; D000499:Allylamine; C029178:naftifine; C067594:butenafine