Ritter reaction-mediated syntheses of 2-oxaadamantan-5-amine, a novel amantadine analog

Rosana Leiva; Sabrina Gazzarrini; Roser Esplugas; Anna Moroni; Lieve Naesens; Francesc X Sureda; Santiago Vázquez

doi:10.1016/j.tetlet.2015.01.160

Ritter reaction-mediated syntheses of 2-oxaadamantan-5-amine, a novel amantadine analog

Tetrahedron Lett. 2015 Mar 4;56(10):1272-1275. doi: 10.1016/j.tetlet.2015.01.160. Epub 2015 Jan 31.

Authors

Rosana Leiva¹, Sabrina Gazzarrini², Roser Esplugas³, Anna Moroni², Lieve Naesens⁴, Francesc X Sureda³, Santiago Vázquez¹

Affiliations

¹ Laboratori de Química Farmacèutica (Unitat Associada al CSIC), Facultat de Farmàcia, and Institute of Biomedicine (IBUB), Universitat de Barcelona, Av. Joan XXIII, s/n, Barcelona E-08028, Spain.
² Department of Biosciences and National Research Council (CNR) Biophysics Institute (IBF), University of Milan, Via Celoria 26, 20133 Milan, Italy.
³ Unitat de Farmacologia, Facultat de Medicina i Ciències de la Salut, Universitat Rovira i Virgili, c./ St. Llorenç 21, Reus E-43201, Spain.
⁴ Rega Institute for Medical Research, KU Leuven, 3000 Leuven, Belgium.

Abstract

Two alternative syntheses of 2-oxaadamantan-5-amine, a novel analog of the clinically approved drug amantadine, are reported. The compound has been tested as an anti-influenza A virus agent and as an NMDA receptor antagonist. While the compound was not antivirally active, it displayed moderate activity as an NMDA receptor antagonist.

Keywords: Adamantane; Amantadine; M2 channel; NMDA receptor antagonist; Ritter reaction.