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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
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 |
| UTAS Author: | Amos, RIJ (Dr Ruth Amos) |
| UTAS Author: | Gourlay, BS (Dr Brendon Gourlay) |
| UTAS Author: | Yates, BF (Professor Brian Yates) |
| UTAS Author: | Lewis, TW (Dr Trevor Lewis) |
| UTAS Author: | Smith, JA (Associate Professor Jason Smith) |
| ID Code: | 88736 |
| Year Published: | 2013 |
| Web of Science® Times Cited: | 8 |
| Deposited By: | Chemistry |
| Deposited On: | 2014-02-13 |
| Last Modified: | 2017-10-25 |
| Downloads: | 108 View Download Statistics |
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