8-aminobicyclo[3.2.1]octanes: synthesis and anti-viral activity

A series of 8-chlorobicyclo[3,2,1]oct-6-enes has been prepared from cyclohe xenyl chlorides and simple alkynes via a one-step [3+2] cycloaddition metho dology. and then converted into the corresponding bicyclic amines. Against influenza-A virus a number of these showed in vitro activity. and amine (2) was comparable to amantadine in vivo. Good activity against influenza-B vi rus was less common, and none of the amines showed high potency against bot h viruses. Amines (20) and (23) showed significant activity versus respirat ory syncytial virus. (C) 2001 Elsevier Science Ltd. All rights reserved.