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Enantiomerically pure 1,3-dioxanes as highly selective NMDA and σ₁ receptor ligands.

Journal of medicinal chemistry (2012-09-28)
Jens Köhler, Klaus Bergander, Jörg Fabian, Dirk Schepmann, Bernhard Wünsch
RESUMEN

We synthesized and investigated the NMDA and σ₁ receptor affinity of enantiomerically pure 2-(2-phenyl-1,3-dioxan-4-yl)ethanamines 17-26. The primary amines (R,R)-18-20 with an axially oriented phenyl moiety in position 2 interacted with high enantioselectivity (eudismic ratios 70-130) and high affinity (K(i)((R,R)-19) = 13 nM) with the PCP binding site of the NMDA receptor. Introduction of an N-benzyl moiety led to potent σ₁ ligands including compound (S,R)-22 (K(i) = 6 nM) with an equatorially oriented phenyl moiety in position 2.

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PCP (Phencyclidine) solution, 1.0 mg/mL in methanol, ampule of 1 mL, certified reference material, Cerilliant®