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Title: Influence of an additional 2-amino substituent of the 1-aminoethyl pharmacophore group on the potency of rimantadine against influenza virus A
Authors: Tataridis, Dimitrios ×
Fytas, George
Kolocouris, Antonios
Fytas, Christos
Kolocouris, Nicolas
Foscolos, George B
Padalko, Elizaveta
Neyts, Johan
De Clercq, Erik #
Issue Date: Feb-2007
Publisher: Pergamon Press
Series Title: Bioorganic & Medicinal Chemistry Letters vol:17 issue:3 pages:692-696
Abstract: We examined whether the incorporation of a second amino group into the 1-aminoethyl pharmacophore of rimantadine 2 and into the piperidine pharmacophore of the heterocyclic rimantadine 4 was compatible with anti-influenza virus A activity. The new synthetic molecules are capable of forming two hydrogen bonds within the receptor. We identified molecules 8 and 16, bearing the adamantyl and 1,2-diaminoethyl groups, which are equipotent to rimantadine 2 bearing the adamantyl and 1-aminoethyl pharmacophore groups. Interestingly, diamino compound 16 is a 4-fold more potent inhibitor than its parent monoamino heterocyclic rimantadine 4 propably because of additional hydrogen bonding interactions with the M2 protein receptor.
URI: 
ISSN: 0960-894X
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Laboratory of Virology and Chemotherapy (Rega Institute)
× corresponding author
# (joint) last author

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