Enantiomerically pure 2-methyltetrahydro-3-benzazepin-1-ols selectively blocking GluN2B subunit containing N-methyl-D-aspartate receptors

…, T Uengwetwanit, F Gaube, T Winckler…

Index: Rook, Yvonne; Schmidtke, Kai-Uwe; Gaube, Friedemann; Schepmann, Dirk; Wuensch, Bernhard; Heilmann, Joerg; Lehmann, Jochen; Winckler, Thomas Journal of Medicinal Chemistry, 2010 , vol. 53, # 9 p. 3611 - 3617

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Citation Number: 4

Abstract

A chiral pool synthesis was developed to obtain all four stereoisomeric 2-methyl-3-(4- phenylbutyl) tetrahydro-3-benzazepin-1-ols 21, 31, and 32 in a seven-to eight-step sequence. The phenols 32 reveal slightly higher GluN2B affinity than the methyl ethers 21. The GluN2B affinity increases in the order (1 R, 2 S)<(1 S, 2 S)<(1 S, 2 R)<(1 R, 2 R). The stereoisomeric phenols (R, R)-32 and (S, R)-32 show the highest GluN2B affinity and the ...