Benzofuranyl 3,5-bis-polyamine derivatives as time-dependent inhibitors of trypanothione reductase

Chris J. Hamilton, Ahilan Saravanamuthu, Alan H. Fairlamb, Ian M. Eggleston (Lead / Corresponding author)

    Research output: Contribution to journalArticle

    27 Citations (Scopus)

    Abstract

    The synthesis and evaluation of 3,5-disubstituted benzofuran derivatives as time-dependent inhibitors of the protozoan oxidoreductase trypanothione reductase are reported. These molecules were designed as simplified mimetics of the naturally occurring spermidine-bridged macrocyclic alkaloid lunarine 1, a known time-dependent inhibitor of trypanothione reductase. In this series of compounds the bis-polyaminoacrylamide derivatives 2-4 were all shown to be competitive inhibitors, but only the bis-4-methyl-piperazin-1-yl-propylacrylamide derivative 4 displayed time-dependent activity. The kinetics of time dependent inactivation of trypanothione reductase by 1 and 4 have been determined and are compared and discussed herein.

    Original languageEnglish
    Pages (from-to)3683-3693
    Number of pages11
    JournalBioorganic and Medicinal Chemistry
    Volume11
    Issue number17
    DOIs
    Publication statusPublished - 15 Aug 2003

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