Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1374960 | Bioorganic & Medicinal Chemistry Letters | 2006 | 5 Pages |
Abstract
Piceatannol (1) was found to be more effective than caffeic acid, an established antinitrosating agent, in inhibiting N-nitrosation of 2,3-diaminonaphthalene. Product analysis of the reaction mixture of 1 (20 μM) with nitrite ions (80 μM) at pH 3.0 and at 37 °C showed conversion to a single major nitration product, (E)-3,3′,4,5′-tetrahydroxy-β-nitrostilbene (2) (68% yield). This would result from an unexpected nitration at the double bond sector via the 4-phenoxyl radical, which was analyzed at the unrestricted DFT level.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Maria De Lucia, Lucia Panzella, Orlando Crescenzi, Alessandra Napolitano, Vincenzo Barone, Marco d’Ischia,