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Reaction of Rosmarinic Acid with Nitrite Ions in Acidic Conditions: Discovery of Nitro- and Dinitrorosmarinic Acids as New Anti-HIV-1 Agents

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Laboratoire de Chimie Organique et Macromoléculaire, UMR CNRS 8009, Université de Lille 1, 59655 Villeneuve d’Ascq, France, Laboratoire de Biotechnologies et Pharmacologie Génétique Appliquée, UMR CNRS 8113, Ecole Normale Supérieure de Cachan, 61 Avenue du Président Wilson, 94235 Cachan, France, and Molecular Medicine, K. U. Leuven and IRC KULAK, Kapucijnenvoer 33, B-3000 Leuven, Flanders, Belgium
* To whom correspondence should be addressed. Phone: +33 320 43 49 39 . Fax: +33 320 33 63 09. E-mail: [email protected]
†Université de Lille 1.
‡Ecole Normale Supérieure de Cachan.
§K. U. Leuven and IRC KULAK.
Cite this: J. Med. Chem. 2008, 51, 8, 2575–2579
Publication Date (Web):March 20, 2008
https://doi.org/10.1021/jm7011134
Copyright © 2008 American Chemical Society
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    Abstract

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    Rosmarinic acid was reacted with nitrite ions under acidic conditions to give 6′-nitro- and 6′,6′′-dinitrorosmarinic acids according to the reaction time. Both compounds were active as HIV-1 integrase inhibitors at the submicromolar level. They also inhibited the viral replication in MT-4 cells with modest and similar selectivity indexes. The nitration of rosmarinic acid strongly improves the anti-integrase inhibition and the antiviral activity without increasing the cellular toxicity.

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