Issue 1, 2013

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

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

Article information

Article type
Review Article
Submitted
29 Jun 2012
Accepted
01 Aug 2012
First published
16 Aug 2012

Med. Chem. Commun., 2013,4, 27-33

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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