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3-Phenyl-5-acyloxymethyl-2H,5H-furan-2-ones:  Synthesis and Biological Activity of a Novel Group of Potential Antifungal Drugs

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    3-Phenyl-5-acyloxymethyl-2H,5H-furan-2-ones:  Synthesis and Biological Activity of a Novel Group of Potential Antifungal Drugs†
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    Laboratory of Structure and Interactions of Biologically Active Molecules, Department of Inorganic and Organic Chemistry, Faculty of Pharmacy, Charles University, Heyrovského 1203, CZ-500 05 Hradec Králové, Czech Republic, Department of Biological and Medical Sciences, Faculty of Pharmacy, Charles University, Heyrovského 1203, CZ-500 05 Hradec Králové, Czech Republic, Department of Pharmacology and Toxicology, Faculty of Pharmacy, Charles University, Heyrovského 1203, CZ-500 05 Hradec Králové, Czech Republic, and Research Centre LN00B125, Heyrovského 1203, CZ-500 05 Hradec Králové, Czech Republic
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    Journal of Medicinal Chemistry

    Cite this: J. Med. Chem. 2001, 44, 17, 2701–2706
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    https://doi.org/10.1021/jm010155x
    Published July 21, 2001
    Copyright © 2001 American Chemical Society
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    Abstract

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    3-(Substituted phenyl)-5-acyloxymethyl-2H,5H-furan-2-ones related to the natural product (−)incrustoporine were synthesized and their in vitro antifungal activity evaluated. The compounds with halogen substituents on the phenyl ring displayed much higher antifungal effect against Aspergillus fumigatus than selected representatives of azole antifungal drugs. In particular, the activity (1.34 μg/mL) of the most promising derivative, 3-(3,4-dichlorophenyl)-5-pivaloyloxymethyl-2H,5H-furan-2-one, was comparable to that of amphotericin B (0.5 μg/mL). Preliminary evaluation of the toxicity of the compound was carried out as well. Considering the size and properties of these molecules in comparison with those of amphotericin B, further development of this novel group of antifungals may lead to substances with better pharmacological profiles than that of the standard anti-Aspergillus drug.

    Copyright © 2001 American Chemical Society

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    †

     Dedicated to Professor Karel Waisser on the occasion of his 65th birthday.

    *

     To whom correspondence should be addressed. Phone:  +420-49-5067277. Fax:  +420-49-5210002. E-mail:  [email protected].

    ‡

     Laboratory of Structure and Interactions of Biologically Active Molecules, Charles University.

    §

     Department of Biological and Medical Sciences, Charles University.

    ‖

     Department of Pharmacology and Toxicology, Charles University.

    ⊥

     Research Centre LN00B125.

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    Journal of Medicinal Chemistry

    Cite this: J. Med. Chem. 2001, 44, 17, 2701–2706
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    https://doi.org/10.1021/jm010155x
    Published July 21, 2001
    Copyright © 2001 American Chemical Society
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