| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1362205 | Bioorganic & Medicinal Chemistry Letters | 2011 | 4 Pages |
The electrophilic reactivity of the bioactive marine sponge natural product halenaquinone has been investigated by reaction with the biomimetic nucleophiles N-acetyl-l-cysteine and Nα-acetyl-l-lysine. While cysteine reacted at the vacant quinone positions C-14 and C-15, lysine was found to react preferentially at the keto-furan position C-1. A small library of analogues was prepared by reaction of halenaquinone with primary amines, and evaluated against a range of biological targets including phospholipase A2, farnesyltransferases (FTases) and Plasmodium falciparum. Geranylamine analogue 11 exhibited the most potent activity towards FTases (IC50 0.017–0.031 μM) and malaria (IC50 0.53–0.62 μM).
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