%0 Journal Article %J Journal of medicinal chemistry %D 2001 %T Synthesis, in vitro pharmacology, and molecular modeling of syn-huprines as acetylcholinesterase inhibitors %A Camps,P. %A Gomez,E. %A Munoz-Torrero,D. %A Badia,A. %A Vivas,N. M. %A Barril, Xavier %A M. Orozco %A F. J. Luque %K Acetylcholinesterase/metabolism; Aminoquinolines/chemical synthesis/chemistry; Animals; Cattle; Cholinesterase Inhibitors/chemical synthesis/chemistry; Heterocyclic Compounds with 4 or More Rings/chemical synthesis/chemistry; Humans; Models %K Molecular; Stereoisomerism; Structure-Activity Relationship %N 26 %P 4733 - 4736 %V 44 %X Two 12-amino-6,7,8,11-tetrahydro-7,11-methanocycloocta[b]quinoline derivatives [9-Me(Et)] (syn-huprines) have been obtained by condensation of known 7-alkylbicyclo[3.3.1]non-6-en-3-ones with 2-(trifluoromethyl)aniline, followed by basic cyclization of the resulting imine, and chromatographic separation of the regioisomeric mixture of products, thus obtained. The new (+/-)-syn-huprines were shown to be slightly less active bovine or human acetylcholinesterase inhibitors than the corresponding anti-derivatives. Molecular modeling simulations allow us to explain the differences in inhibitory activity of these compounds on the basis of an inverse solvation effect. %8 2001/12/20/