Journal of medicinal chemistry, 2001-12, Vol.44 (26), p.4733-4736
2001
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Details
- Autor(en) / Beteiligte
- Titel
- Synthesis, in Vitro Pharmacology, and Molecular Modeling of syn-Huprines as Acetylcholinesterase Inhibitors
- Ist Teil von
- Journal of medicinal chemistry, 2001-12, Vol.44 (26), p.4733-4736
- Ort / Verlag
- Washington, DC: American Chemical Society
- Erscheinungsjahr
- 2001
- Quelle
- MEDLINE
- Beschreibungen/Notizen
- 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.
- Sprache
- Englisch
- Identifikatoren
- ISSN: 0022-2623eISSN: 1520-4804DOI: 10.1021/jm010949bTitel-ID: cdi_proquest_miscellaneous_72366672
- Format
- –
- Schlagworte
- Acetylcholinesterase - metabolism, Aminoquinolines - chemical synthesis, Aminoquinolines - chemistry, Animals, Biological and medical sciences, Cattle, Cholinesterase Inhibitors - chemical synthesis, Cholinesterase Inhibitors - chemistry, Heterocyclic Compounds, 4 or More Rings - chemical synthesis, Heterocyclic Compounds, 4 or More Rings - chemistry, Humans, Medical sciences, Models, Molecular, Neuropharmacology, Pharmacology. Drug treatments, Psychoanaleptics: cns stimulant, antidepressant agent, nootropic agent, mood stabilizer..., (alzheimer disease), Psychology. Psychoanalysis. Psychiatry, Psychopharmacology, Stereoisomerism, Structure-Activity Relationship