Novel 3-(2-Adamantyl) pyrrolidines with potent activity against influenza A virus—identification of aminoadamantane derivatives bearing two pharmacophoric amine …

G Stamatiou, A Kolocouris, N Kolocouris…

Index: Stamatiou, George; Kolocouris, Antonios; Kolocouris, Nicolas; Fytas, George; Foscolos, George B; Neyts, Johan; De Clercq, Erik Bioorganic and Medicinal Chemistry Letters, 2001 , vol. 11, # 16 p. 2137 - 2142

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Citation Number: 57

Abstract

The 3-(2-adamantyl) pyrrolidines 8a–g, 14 were synthesized and evaluated for activity against influenza A virus. The parent N–H compound 14 was several times more active than amantadine against H2N2 and H3N2 influenza A virus. The combined use of NMR spectroscopy and computational chemistry showed that the conformation around the pyrrolidine–adamantyl carbon–carbon bond is trans and the pyrrolidine heterocycle has ...