3-Phenyl-5-methyl-2H, 5H-furan-2-ones: tuning antifungal activity by varying substituents on the phenyl ring

M Pour, M Špulák, V Balšánek, J Kuneš… - Bioorganic & medicinal …, 2000 - Elsevier
M Pour, M Špulák, V Balšánek, J Kuneš, V Buchta, K Waisser
Bioorganic & medicinal chemistry letters, 2000Elsevier
A series of racemic 3-phenyl-5-methyl-2H, 5H-furan-2-ones related to a natural product,(−)
incrustoporine, was synthesized, and their antifungal activity evaluated. The key structural
feature, furanone ring, was closed via H2SO4-mediated cyclization of 2-phenylpent-4-enoic
acids. The compounds displayed antifungal activity, especially against filamentous fungi.
Expressed as the minimum inhibition concentration (MIC) in μmol/L, the activity of the most
promising derivative against Absidia corymbifera matched that of ketoconazole (31.25 …
A series of racemic 3-phenyl-5-methyl-2H,5H-furan-2-ones related to a natural product, (−)incrustoporine, was synthesized, and their antifungal activity evaluated. The key structural feature, furanone ring, was closed via H2SO4-mediated cyclization of 2-phenylpent-4-enoic acids. The compounds displayed antifungal activity, especially against filamentous fungi. Expressed as the minimum inhibition concentration (MIC) in μmol/L, the activity of the most promising derivative against Absidia corymbifera matched that of ketoconazole (31.25μmol/L). In terms of μg/mL, the substance was more active (7.6μg/mL) than this standard antifungal drug (16.6μg/mL).
Elsevier
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