Synthesis of 2-(2-adamantyl)piperidines and structure anti-influenza virus a activity relationship study using a combination of NMR spectroscopy and molecular modeling

✍ Scribed by Antonios Kolocouris; Dimitrios Tataridis; George Fytas; Thomas Mavromoustakos; George B. Foscolos; Nicolas Kolocouris; Erik De Clercq

• Publisher: Elsevier Science
• Year: 1999
• Tongue: English
• Weight: 456 KB
• Volume: 9
• Category: Article
• ISSN: 0960-894X
• DOI: 10.1016/s0960-894x(99)00631-9

✦ Synopsis

The 2-(2-adamantyl)piperidines 13 and 15a-e were synthesized and evaluated for anti-influenza virus A and B activity. The parent N-H compound 13 was 3-4 times more active than amantadine and rimantadine against H2N 2 influenza A. N-alkylation of 13 resulted in derivatives 15a-e that were devoid of biological activity. This dramatic reduction in biological activity may be attributed to the different conformational properties between N-H and N-alkyl piperidines, as deduced from the combination of computational chemistry and NMR spectroscopy.