Selectivity of sterically fixed tryptamine and 5-methoxytryptamine derivatives for serotonin receptor subtypes, I: Synthesis of N-alkyl- and N,N-dialkyl-3-indolylbicyclo[2.2.1]heptane-2-amines.
Twenty-six title compounds with the ethylamine part of tryptamine or 5-methoxytryptamine fixed in an anticlinal ecliptic conformation were synthesized for assaying them at the different known serotonin receptors. Several alkylation methods have been improved and adapted for the space consuming norbornane system. The structures were fully elucidated by high-field NMR spectroscopy. All 1H- and 13C-signals could be assigned by means of 1H-1H- and 13C-1H-correlation spectroscopy (COSY).
Rehse
K
K
Institut für Pharmazie, Freien Universität Berlin, Germany.
Zimmermann
H
H
D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D007211:Indoles / Q000138:chemical synthesis* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D011985:Receptors, Serotonin / Q000187:drug effects*
D001643:Bridged Bicyclo Compounds; D007211:Indoles; D011985:Receptors, Serotonin