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. Author manuscript; available in PMC: 2014 May 8.
Published in final edited form as: Chem Rev. 2013 Feb 25;113(5):3516–3604. doi: 10.1021/cr100264t

Scheme 10.

Scheme 10

Refinement of adamantyl amines and -diamines targeting the Influenza A M2 ion channel. Numbers in parentheses are the relative potencies of the compounds measured as an x-fold increase or decrease in MIC50 compared to amantadine as positive control. 64 – 68: Influenza A (Ishikawa); 69 – 75: Influenza A2/Japan/305/1957 (H2N2). All compounds screened in MDCK cell culture assays.