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Issue 17, 2014
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Benzofuranquinones as inhibitors of indoleamine 2,3-dioxygenase (IDO). Synthesis and biological evaluation

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Abstract

A series of benzofuranquinones, analogues of the marine metabolite annulin A, has been synthesized and evaluated as inhibitors of human indoleamine 2,3-dioxygenase (IDO). The synthesis was carried out by copper(II)-mediated reaction of bromobenzoquinones with 1,3-dicarbonyl compounds followed by functional group interconversions. The most potent compounds were 5-methoxy-2-methylbenzofuranquinones containing a CH2OR group at position-3 with IC50 ∼ 0.2 mM. The corresponding hydroquinones were inactive. Compounds based on the benzimidazolequinone framework are also active IDO inhibitors. The quinones do not generate significant levels of oxidative stress at concentrations that inhibit IDO.

Graphical abstract: Benzofuranquinones as inhibitors of indoleamine 2,3-dioxygenase (IDO). Synthesis and biological evaluation

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Publication details

The article was received on 13 Nov 2013, accepted on 20 Feb 2014 and first published on 21 Feb 2014


Article type: Paper
DOI: 10.1039/C3OB42258E
Citation: Org. Biomol. Chem., 2014,12, 2663-2674
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    Benzofuranquinones as inhibitors of indoleamine 2,3-dioxygenase (IDO). Synthesis and biological evaluation

    C. Carvalho, D. Siegel, M. Inman, R. Xiong, D. Ross and C. J. Moody, Org. Biomol. Chem., 2014, 12, 2663
    DOI: 10.1039/C3OB42258E

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