Issue 1, 2013
From the journal:

Organic & Biomolecular Chemistry

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

Ruth I. J. Amos,ab   Brendon S. Gourlay,a   Brian F. Yates,a   Carl H. Schiesser,bc   Trevor W. Lewisa  and  Jason A. Smith*ab  

* Corresponding authors

a School of Chemistry, University of Tasmania, Hobart, Australia
E-mail: Jason.Smith@utas.edu.au
Fax: +613 6226 2858
Tel: +613 6226 2182

b Australian Research Council Centre of Excellence for Free Radical Chemistry and Biotechnology, Australia

c School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne, Victoria, Australia

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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Article information

DOI
https://doi.org/10.1039/C2OB26419F
Article type
Paper
Submitted
20 Jul 2012
Accepted
08 Nov 2012
First published
08 Nov 2012

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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