Synthesis, in vitro pharmacology, and molecular modeling of syn-huprines as acetylcholinesterase inhibitors

P. Camps, E. Gómez, D. Muñoz-Torrero, A. Badia, N. M. Vivas, X. Barril, M. Orozco, F. J. Luque

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53 Citations (Scopus)

Abstract

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.
Original languageEnglish
Pages (from-to)4733-4736
JournalJournal of Medicinal Chemistry
Volume44
DOIs
Publication statusPublished - 20 Dec 2001

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