Novel high energy intermediate analogues with triazasterol-related structures as inhibitors of ergosterol biosynthesis. Part I: synthesis and antifungal activity of N-alkyl-N'-(phenethyl- and cyclohexenylethyl)guanidines and N2-substituted 2-imidazolinamines.
A series of N-alkyl-N'-(phenethyl- and cyclohexenylethyl) guanidines and N(2)- and N(2), 4-substituted imidazolin-2-amine hydrochlorides with triazasterol-related structures was designed and synthesized as stable analogues to mimic high energy intermediates of ergosterol biosynthesis. The in vitro antifungal susceptibility tests with a standard panel of pathogenic fungi revealed moderate to strong antimycotic effects of the sixteen prepared compounds, in some cases comparable with the activity observed for itraconazole.
Gössnitzer
Edith
E
Institute of Pharmaceutical Chemistry and Pharmaceutical Technology, Karl-Franzens-University Graz, Schubertstrasse 1, A-8010 Graz, Austria. edith.goessnitzer@uni-graz.at
Malli
Roland
R
Schuster
Silvia
S
Favre
Bertrand
B
Ryder
Neil S
NS
D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D004875:Ergosterol / Q000096:biosynthesis; D005658:Fungi / Q000187:drug effects; D006146:Guanidines / Q000138:chemical synthesis* / Q000494:pharmacology; D007093:Imidazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D013329:Structure-Activity Relationship
D000935:Antifungal Agents; D006146:Guanidines; D007093:Imidazoles; D004875:Ergosterol