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Crystal structure of (1S*,2R*)-7-benzyloxy-2-methyl-3-tosyl-2,3,4,5-tetrahydro-1H-3-benzazepin-1-ol: elucidation of the relative configuration of potent allosteric GluN2B selective NMDA receptor antagonists
In the title compound, C(25)H(27)NO(4)S, which crystallized as a racemate, the relative configuration of the adjacent OH and CH(3) 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 tosylate moiety are incli...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2016
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4908544/ https://www.ncbi.nlm.nih.gov/pubmed/27308018 http://dx.doi.org/10.1107/S2056989016005855 |
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author | Tewes, Bastian Frehland, Bastian Fröhlich, Roland Wünsch, Bernhard |
author_facet | Tewes, Bastian Frehland, Bastian Fröhlich, Roland Wünsch, Bernhard |
author_sort | Tewes, Bastian |
collection | PubMed |
description | In the title compound, C(25)H(27)NO(4)S, which crystallized as a racemate, the relative configuration of the adjacent OH and CH(3) 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 tosylate 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, molecules 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 interactions, forming a three-dimensional architecture. |
format | Online Article Text |
id | pubmed-4908544 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-49085442016-06-15 Crystal structure of (1S*,2R*)-7-benzyloxy-2-methyl-3-tosyl-2,3,4,5-tetrahydro-1H-3-benzazepin-1-ol: elucidation of the relative configuration of potent allosteric GluN2B selective NMDA receptor antagonists Tewes, Bastian Frehland, Bastian Fröhlich, Roland Wünsch, Bernhard Acta Crystallogr E Crystallogr Commun Research Communications In the title compound, C(25)H(27)NO(4)S, which crystallized as a racemate, the relative configuration of the adjacent OH and CH(3) 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 tosylate 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, molecules 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 interactions, forming a three-dimensional architecture. International Union of Crystallography 2016-04-15 /pmc/articles/PMC4908544/ /pubmed/27308018 http://dx.doi.org/10.1107/S2056989016005855 Text en © Tewes et al. 2016 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. |
spellingShingle | Research Communications Tewes, Bastian Frehland, Bastian Fröhlich, Roland Wünsch, Bernhard Crystal structure of (1S*,2R*)-7-benzyloxy-2-methyl-3-tosyl-2,3,4,5-tetrahydro-1H-3-benzazepin-1-ol: elucidation of the relative configuration of potent allosteric GluN2B selective NMDA receptor antagonists |
title | Crystal structure of (1S*,2R*)-7-benzyloxy-2-methyl-3-tosyl-2,3,4,5-tetrahydro-1H-3-benzazepin-1-ol: elucidation of the relative configuration of potent allosteric GluN2B selective NMDA receptor antagonists |
title_full | Crystal structure of (1S*,2R*)-7-benzyloxy-2-methyl-3-tosyl-2,3,4,5-tetrahydro-1H-3-benzazepin-1-ol: elucidation of the relative configuration of potent allosteric GluN2B selective NMDA receptor antagonists |
title_fullStr | Crystal structure of (1S*,2R*)-7-benzyloxy-2-methyl-3-tosyl-2,3,4,5-tetrahydro-1H-3-benzazepin-1-ol: elucidation of the relative configuration of potent allosteric GluN2B selective NMDA receptor antagonists |
title_full_unstemmed | Crystal structure of (1S*,2R*)-7-benzyloxy-2-methyl-3-tosyl-2,3,4,5-tetrahydro-1H-3-benzazepin-1-ol: elucidation of the relative configuration of potent allosteric GluN2B selective NMDA receptor antagonists |
title_short | Crystal structure of (1S*,2R*)-7-benzyloxy-2-methyl-3-tosyl-2,3,4,5-tetrahydro-1H-3-benzazepin-1-ol: elucidation of the relative configuration of potent allosteric GluN2B selective NMDA receptor antagonists |
title_sort | crystal structure of (1s*,2r*)-7-benzyloxy-2-methyl-3-tosyl-2,3,4,5-tetrahydro-1h-3-benzazepin-1-ol: elucidation of the relative configuration of potent allosteric glun2b selective nmda receptor antagonists |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4908544/ https://www.ncbi.nlm.nih.gov/pubmed/27308018 http://dx.doi.org/10.1107/S2056989016005855 |
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