In vitro antifungal activity of 3-phenyl-2H-benzoxazine-2,4(3H)-diones.
A series of 81 3-phenyl-2H-benzoxazine-2,4(3H)-diones with substitution at C(6) on the benzoxazine ring and on the phenyl moiety was synthesized; the compounds were evaluated for antifungal activity against five strains of potentially pathogenic fungi (Absidia corymbifera, Aspergillus fumigatus, Candida albicans, Microsporum gypseum and Trichophyton mentagrophytes). Structure-activity relationships against T. mentagrophytes and M. gypseum were determined using the Free-Wilson method, which was further combined with the approach of Hansch. In vitro antifungal activity becomes higher with increasing electron-accepting ability of the substituents on the phenyl ring, and with increasing lipophilicity.
Waisser
K
K
Department of Inorganic and Organic Chemistry, Charles University, Faculty of Pharmacy, 500 05 Hradec Králové, Czechia. waisser@faf.cuni.cz
Kubicová
L
L
Buchta
V
V
Kubanová
P
P
Bajerová
K
K
Jirásková
L
L
Bednarík
O
O
Bures
O
O
Holý
P
P
D000935:Antifungal Agents / Q000494:pharmacology*; D005658:Fungi / Q000187:drug effects*; D006801:Humans; D008826:Microbial Sensitivity Tests; D010078:Oxazines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship
D000935:Antifungal Agents; D010078:Oxazines