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

Citation

Amos, RIJ and Gourlay, BS and Yates, BF and Schiesser, CH and Lewis, TW and Smith, JA, Mechanistic investigation of the oxidation of hydrazides: implications for the activation of the TB drug isoniazid, Organic and Biomolecular Chemistry, 11, (1) pp. 170-176. ISSN 1477-0520 (2013) [Refereed Article]


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Copyright Statement

Copyright 2013 Royal Society of Chemistry

DOI: doi:10.1039/c2ob26419f

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.

Item Details

Item Type:Refereed Article
Research Division:Chemical Sciences
Research Group:Organic Chemistry
Research Field:Free Radical Chemistry
Objective Division:Expanding Knowledge
Objective Group:Expanding Knowledge
Objective Field:Expanding Knowledge in the Chemical Sciences
Author:Amos, RIJ (Dr Ruth Amos)
Author:Gourlay, BS (Dr Brendon Gourlay)
Author:Yates, BF (Professor Brian Yates)
Author:Lewis, TW (Dr Trevor Lewis)
Author:Smith, JA (Associate Professor Jason Smith)
ID Code:88736
Year Published:2013
Web of Science® Times Cited:6
Deposited By:Chemistry
Deposited On:2014-02-13
Last Modified:2016-12-19
Downloads:64 View Download Statistics

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