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6-Amino-1-benzyl-4-(4-chlorophenyl)-3-(4-pyridyl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
The crystal structure of the title compound, C(25)H(18)ClN(5)O, was determined in the course of our studies on the synthesis of 1,4-dihydropyrano[2,3-c]pyrazole as an inhibitor of the p38 mitogen-activated protein kinase (MAPK). The compound was prepared via a base-catalysed synthesis from 1-benzyl...
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Formato: | Texto |
Lenguaje: | English |
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International Union of Crystallography
2008
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2960986/ https://www.ncbi.nlm.nih.gov/pubmed/21202092 http://dx.doi.org/10.1107/S160053680800487X |
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author | Lehmann, Frank Schollmeyer, Dieter Laufer, Stefan |
author_facet | Lehmann, Frank Schollmeyer, Dieter Laufer, Stefan |
author_sort | Lehmann, Frank |
collection | PubMed |
description | The crystal structure of the title compound, C(25)H(18)ClN(5)O, was determined in the course of our studies on the synthesis of 1,4-dihydropyrano[2,3-c]pyrazole as an inhibitor of the p38 mitogen-activated protein kinase (MAPK). The compound was prepared via a base-catalysed synthesis from 1-benzyl-3-(4-pyridyl)-1H-pyrazol-5(4H)-one with p-chloroaldehyde and malononitrile. The crystal data obtained were used to generate a three-dimensional pharmacophore model for in silico database screening. The phenyl ring is disordered over two positions, with site occupancy factors of 0.55 and 0.45. The dihedral angles between the 1,4-dihydropyrano[2,3-c]pyrazole unit and the chlorophenyl and pyridine rings are 83.7 (1) and 16.0 (1)°, respectively. The chlorophenyl and pyridine rings make a dihedral angle of 86.8 (2)°. |
format | Text |
id | pubmed-2960986 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2008 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-29609862010-12-30 6-Amino-1-benzyl-4-(4-chlorophenyl)-3-(4-pyridyl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile Lehmann, Frank Schollmeyer, Dieter Laufer, Stefan Acta Crystallogr Sect E Struct Rep Online Organic Papers The crystal structure of the title compound, C(25)H(18)ClN(5)O, was determined in the course of our studies on the synthesis of 1,4-dihydropyrano[2,3-c]pyrazole as an inhibitor of the p38 mitogen-activated protein kinase (MAPK). The compound was prepared via a base-catalysed synthesis from 1-benzyl-3-(4-pyridyl)-1H-pyrazol-5(4H)-one with p-chloroaldehyde and malononitrile. The crystal data obtained were used to generate a three-dimensional pharmacophore model for in silico database screening. The phenyl ring is disordered over two positions, with site occupancy factors of 0.55 and 0.45. The dihedral angles between the 1,4-dihydropyrano[2,3-c]pyrazole unit and the chlorophenyl and pyridine rings are 83.7 (1) and 16.0 (1)°, respectively. The chlorophenyl and pyridine rings make a dihedral angle of 86.8 (2)°. International Union of Crystallography 2008-03-12 /pmc/articles/PMC2960986/ /pubmed/21202092 http://dx.doi.org/10.1107/S160053680800487X Text en © Lehmann et al. 2008 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 | Organic Papers Lehmann, Frank Schollmeyer, Dieter Laufer, Stefan 6-Amino-1-benzyl-4-(4-chlorophenyl)-3-(4-pyridyl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile |
title | 6-Amino-1-benzyl-4-(4-chlorophenyl)-3-(4-pyridyl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile |
title_full | 6-Amino-1-benzyl-4-(4-chlorophenyl)-3-(4-pyridyl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile |
title_fullStr | 6-Amino-1-benzyl-4-(4-chlorophenyl)-3-(4-pyridyl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile |
title_full_unstemmed | 6-Amino-1-benzyl-4-(4-chlorophenyl)-3-(4-pyridyl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile |
title_short | 6-Amino-1-benzyl-4-(4-chlorophenyl)-3-(4-pyridyl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile |
title_sort | 6-amino-1-benzyl-4-(4-chlorophenyl)-3-(4-pyridyl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2960986/ https://www.ncbi.nlm.nih.gov/pubmed/21202092 http://dx.doi.org/10.1107/S160053680800487X |
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