Are the 2-isomers of the drug rimantadine active anti-influenza A agents?
There is a lack of information in the medical chemistry literature concerning the anti-influenza A activity of the drug rimantadine's 2-isomer (2-rimantadine). We now present results showing that, although 2-adamantanamine (2-amantadine) 3 is only moderately active, some 2-rimantadine analogues are effective anti-influenza A virus agents in vitro. The 2-rimantadine analogues and their spirocyclobutane and spirocyclopentane congeners were synthesized through interesting routes. The 2-rimantadine analogues were 2-4 times more potent than rimantadine 2 against influenza virus A H2N2 strain; their spirocyclobutane congeners proved equally active to rimantadine 2. Two compounds exhibited a similar activity and one of the compounds was was fourfold more potent than rimantadine 2 against H3N2 strain.
Zoidis
Grigoris
G
Department of Pharmacy, Division of Pharmaceutical Chemistry, University of Athens, Athens, Greece.
Kolocouris
Nicolas
N
Foscolos
George B
GB
Kolocouris
Antonios
A
Fytas
George
G
Karayannis
P
P
Padalko
Elizaveta
E
Neyts
Johan
J
De Clercq
Erik
E
D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D002478:Cells, Cultured / Q000187:drug effects; D009980:Influenza A virus / Q000187:drug effects*; D009981:Influenza B virus / Q000187:drug effects; D007536:Isomerism; D008826:Microbial Sensitivity Tests; D008956:Models, Chemical; D012299:Rimantadine / Q000031:analogs & derivatives* / Q000494:pharmacology / Q000633:toxicity; D013329:Structure-Activity Relationship
D000998:Antiviral Agents; D012299:Rimantadine