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  • Inhibition of carbonic anhydrase isozymes I, II and IX with benzenesulfonamides containing an organometallic moiety.

    Author(s)
    Salmon, Adam J
    Williams, Michael L
    Innocenti, Alessio
    Vullo, Damela
    Supuran, Claudiu T
    Poulsen, Sally-Ann
    Griffith University Author(s)
    Poulsen, Sally-Ann
    Year published
    2007
    Metadata
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    Abstract
    A novel series of benzenesulfonamides that contain ferrocenyl or ruthenocenyl moieties were synthesized and investigated for their ability to inhibit the enzymatic activity of physiologically relevant carbonic anhydrase (CA) isozymes: hCA I, II and tumour-associated IX (h = human). This manuscript describes the regioselective synthesis of both the 1,4- and 1,5-disubstituted-1,2,3-triazole benzenesulfonamides from ethnylmetallocene substrates This is the first report describing the covalent attachment of organometallic moieties to the arylsulfonamide (ArSO2NH2) CA recognition pharmacophore. At hCA I these metallocene derivatives ...
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    A novel series of benzenesulfonamides that contain ferrocenyl or ruthenocenyl moieties were synthesized and investigated for their ability to inhibit the enzymatic activity of physiologically relevant carbonic anhydrase (CA) isozymes: hCA I, II and tumour-associated IX (h = human). This manuscript describes the regioselective synthesis of both the 1,4- and 1,5-disubstituted-1,2,3-triazole benzenesulfonamides from ethnylmetallocene substrates This is the first report describing the covalent attachment of organometallic moieties to the arylsulfonamide (ArSO2NH2) CA recognition pharmacophore. At hCA I these metallocene derivatives were either nanomolar or low micromolar inhibitors, while against hCA II and IX inhibition in the range of 9.7-80 nM and 10.3-85 nM, respectively was observed. The ruthenocenyl derivatives gave superior CA inhibition compared to the ferrocenyl compounds across all three CA isozymes. These compounds constitute a new organometallic class of CA inhibitors with promising biological activity.
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    Journal Title
    Bioorganic & Medicinal Chemistry Letters
    Volume
    17
    Publisher URI
    http://www.elsevier.com/wps/find/journaldescription.cws_home/972/description#description
    DOI
    https://doi.org/10.1016/j.bmcl.2007.07.024
    Subject
    Medicinal and biomolecular chemistry
    Organic chemistry
    Pharmacology and pharmaceutical sciences
    Publication URI
    http://hdl.handle.net/10072/18266
    Collection
    • Journal articles

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