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.

Department of Inorganic and Organic Chemistry Charles University Faculty of Pharmacy 500 05 Hradec Králové Czechia

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Arch Pharm (Weinheim). 1998 Jan;331(1):3-6 PubMed

J Med Chem. 2001 Aug 16;44(17):2701-6 PubMed

Cesk Farm. 1993 Oct;42(5):218-22 PubMed

J Med Chem. 1971 Feb;14(2):148-52 PubMed

Bioorg Med Chem Lett. 2000 Aug 21;10(16):1893-5 PubMed

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