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Issue 1, 2013
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Amino-derivatives of the sesquiterpene lactone class of natural products as prodrugs

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Abstract

The sesquiterpene lactone class of natural products displays a diverse array of biological activities due to the presence of the α-methylene-γ-lactone motif. However, clinical translation of this class has been hampered by poor aqueous solubility and non-selective binding as a Michael acceptor at undesired targets. A prodrug approach has been developed to overcome these problems in which an amine is added into the α-methylene-γ-lactone to mask this group from nucleophiles and increase solubility. The medicinal chemistry of amino-derivatives of the sesquiterpene lactones is described, beginning with synthetic development, moving into pharmacological applications, and finishing with clinical translation.

Graphical abstract: Amino-derivatives of the sesquiterpene lactone class of natural products as prodrugs

  • This article is part of the themed collection: New Talent
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Publication details

The article was received on 29 Jun 2012, accepted on 01 Aug 2012 and first published on 16 Aug 2012


Article type: Review Article
DOI: 10.1039/C2MD20172K
Med. Chem. Commun., 2013,4, 27-33

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    Amino-derivatives of the sesquiterpene lactone class of natural products as prodrugs

    J. R. Woods, H. Mo, A. A. Bieberich, T. Alavanja and D. A. Colby, Med. Chem. Commun., 2013, 4, 27
    DOI: 10.1039/C2MD20172K

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