Crystal structure of (1S*,2R*)-7-benz-yloxy-2-methyl-3-tosyl-2,3,4,5-tetra-hydro-1H-3-benz-azepin-1-ol: elucidation of the relative configuration of potent allosteric GluN2B selective NMDA receptor antagonists

Bastian Tewes; Bastian Frehland; Roland Fröhlich; Bernhard Wünsch

doi:10.1107/S2056989016005855

Crystal structure of (1S,2R)-7-benz-yloxy-2-methyl-3-tosyl-2,3,4,5-tetra-hydro-1H-3-benz-azepin-1-ol: elucidation of the relative configuration of potent allosteric GluN2B selective NMDA receptor antagonists

Acta Crystallogr E Crystallogr Commun. 2016 Apr 15;72(Pt 5):683-6. doi: 10.1107/S2056989016005855. eCollection 2016 May 1.

Authors

Bastian Tewes¹, Bastian Frehland¹, Roland Fröhlich², Bernhard Wünsch³

Affiliations

¹ Institut für Pharmazeutische und Medizinische Chemie der Universität Münster, Corrensstrasse 48, D-48149 Münster, Germany.
² Organisch-chemisches Institut der Westfälischen Wilhelms-Universität Münster, Corrensstr. 40, D-48149-Münster, Germany.
³ Institut für Pharmazeutische und Medizinische Chemie der Universität Münster, Corrensstrasse 48, D-48149 Münster, Germany; Cells-in-Motion Cluster of Excellence (EXC 1003 - CiM), Universität Münster, Germany.

Abstract

In the title compound, C25H27NO4S, which crystallized as a racemate, the relative configuration of the adjacent OH and CH3 groups on the azepine ring is trans. The seven-membered azepin ring has a chair-like conformation. The planar aromatic rings of the benzyl and tosyl-ate moiety are inclined to the planar 3-benzazepine ring by 78.39 (15) and 77.03 (14)°, respectively, and to each another by 13.82 (15)°. In the crystal, mol-ecules are linked via O-H⋯O and C-H⋯O hydrogen bonds, forming double-stranded chains along the a-axis direction. The chains are linked via C-H⋯π inter-actions, forming a three-dimensional architecture.

Keywords: GluN2B antagonists; NMDA receptor antagonists; conformational restriction; crystal structure; hydrogen bonding; ifenprodil analogs; relative configuration; tetrahydro-3-benzazepines.