Synthesis and structure-activity relationships of naftifine-related allylamine antimycotics.
Naftifine (1) is the first representative of the new antifungal allylamine derivatives. Its biological activity is strictly bound to specific structural requirements that are unrelated to those of known antifungals. A tertiary allylamine function seems to be a prerequisite for activity against fungi. By systematic variation of the individual structural elements in 1, detailed structure-activity relationships are defined in which the phenyl ring is the structural feature permitting the widest variations. Versatile synthetic routes to allylamine derivatives and comparative biological data are presented.
D000499:Allylamine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000494:pharmacology / Q000627:therapeutic use; D000588:Amines / Q000138:chemical synthesis / Q000494:pharmacology / Q000627:therapeutic use; D000818:Animals; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000494:pharmacology* / Q000627:therapeutic use; D001232:Aspergillus fumigatus / Q000187:drug effects; D002175:Candida / Q000187:drug effects; D055598:Chemical Phenomena; D002621:Chemistry; D004821:Epidermophyton / Q000187:drug effects; D006168:Guinea Pigs; D008864:Microsporum / Q000187:drug effects; D013175:Sporothrix / Q000187:drug effects; D013329:Structure-Activity Relationship; D014005:Tinea / Q000188:drug therapy; D014249:Trichophyton / Q000187:drug effects
D000588:Amines; D000935:Antifungal Agents; D000499:Allylamine; C029178:naftifine