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Issue 1, 2013
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Mechanistic investigation of the oxidation of hydrazides: implications for the activation of the TB drug isoniazid

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Abstract

Aryl hydrazides are oxidised to acyl radicals through a mechanism involving diimide intermediates that are prone to nucleophilic acyl substitution. This oxidation occurs regardless of the oxidant involved, however there is no evidence that the acyl radical formed undergoes further oxidation to the corresponding acylium ion, even in the presence of strong oxidants. This study may provide insight into the mechanism of isoniazid resistance in Mycobacterium tuberculosis.

Graphical abstract: Mechanistic investigation of the oxidation of hydrazides: implications for the activation of the TB drug isoniazid

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Publication details

The article was received on 20 Jul 2012, accepted on 08 Nov 2012 and first published on 08 Nov 2012


Article type: Paper
DOI: 10.1039/C2OB26419F
Citation: Org. Biomol. Chem., 2013,11, 170-176
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    Mechanistic investigation of the oxidation of hydrazides: implications for the activation of the TB drug isoniazid

    R. I. J. Amos, B. S. Gourlay, B. F. Yates, C. H. Schiesser, T. W. Lewis and J. A. Smith, Org. Biomol. Chem., 2013, 11, 170
    DOI: 10.1039/C2OB26419F

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