- Geometry-affinity relationships of the selective serotonin receptor ligand 9-(aminomethyl)-9,10-dihydroanthracene
-
With the exception of its two aromatic rings and basic nitrogen atom, 9-(aminomethyl)-9,10-dihydroanthracene (AMDA; 1) is remarkably devoid of the pharmacophore features usually associated with high-affinity receptor ligands such as the heteroatom hydrogen bonding features of the endogenous ligand serotonin. AMDA does contain a phenylethylamine skeleton within a tricyclic ring system, and the presence of the second aromatic group is necessary for optimal receptor affinity. The structural requirements for the binding of AMDA at 5-HT2A receptors were investigated with respect to the geometric relationship between the two aromatic rings. It appears that the geometry of the AMDA parent is in the optimal range for fold angle between aromatic moieties. Evaluation of conformationally constrained derivatives of AMDA suggests that a chain extended trans, gauche form is most likely responsible for high affinity.
- Runyon, Scott P.,Peddi, Srinivas,Savage, Jason E.,Roth, Bryan L.,Glennon, Richard A.,Westkaemper, Richard B.
-
p. 1656 - 1664
(2007/10/03)
-
- REACTIONS RETRODIENIQUES-IX. SYNTHESE PAR THERMOLYSE ECLAIR ET ETUDE D'ENAMINES PRIMAIRES INSTABLES
-
Etheneamine 1 and its methyl derivatives 2-7 have been synthesized from the adducts 8-14 by a retro-Diels-Alder reaction under flash thermolytic conditions.The primary enamines 1-4 have been identified (IR, (1)H and (13)C NMR in a pure state at -80 deg C; at the same temperature, the enamines 5-7, less stable, are already accompanied by their tautomeric imines 33 or 34.When warmed up to room temperature, the enamines 1-7 lead, following to their substitution, either to nitrogen heterocycles (30, 42) or to acyclic azadienes (35-37, 39, 40).
- Ripoll, J. L.,Lebrun, H.,Thuillier, A.
-
p. 2497 - 2504
(2007/10/02)
-