908249-11-6Relevant articles and documents
Affinity of?1-aryl-1,2,3,4-tetrahydroisoquinoline derivatives to?the?ion channel binding site of?the?NMDA receptor complex
Ludwig, Matthias,Hoesl, Cornelia E.,H?fner, Georg,Wanner, Klaus T.
, p. 1003 - 1010 (2008/02/09)
A series of 1-aryl-1,2,3,4-tetrahydroisoquinoline and 8-methyl-1-aryl-1,2,3,4-tetrahydroisoquinoline derivatives was evaluated for affinity to the PCP binding site of the NMDA receptor complex. The (S)-configurated tetrahydroisoquinoline derivative (S)-4e·HCl bearing a 2-methylphenyl substituent in position 1 of the heterocyclic ring system and a methyl group in position 8 was found to exhibit the highest affinity among the derivatives with a Ki-value of 0.0374?μM. In addition, this compound shows a remarkable enantioselectivity of binding by being almost 90 times more potent than the corresponding (R)-enantiomer (R)-4e·HCl. Additionally, a convenient and efficient synthetic approach to racemic 1-aryl-1,2,3,4-tetrahydroisoquinoline derivatives is described.