6-Amino-1-benzyl-4-(4-chlorophenyl)-3-(4-pyridyl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile

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, C25H18ClN5O, 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-p...

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Main Authors: Stefan Laufer, Dieter Schollmeyer, Frank Lehmann
Format: Article
Language:English
Published: International Union of Crystallography 2008-04-01
Series:Acta Crystallographica Section E
Online Access:http://scripts.iucr.org/cgi-bin/paper?S160053680800487X
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spelling doaj-e40e0061fdb9495a8249b1244a60d5df2020-11-24T21:27:38ZengInternational Union of CrystallographyActa Crystallographica Section E1600-53682008-04-01644o701o70110.1107/S160053680800487X6-Amino-1-benzyl-4-(4-chlorophenyl)-3-(4-pyridyl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrileStefan LauferDieter SchollmeyerFrank LehmannThe crystal structure of the title compound, C25H18ClN5O, 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)°.http://scripts.iucr.org/cgi-bin/paper?S160053680800487X
collection DOAJ
language English
format Article
sources DOAJ
author Stefan Laufer
Dieter Schollmeyer
Frank Lehmann
spellingShingle Stefan Laufer
Dieter Schollmeyer
Frank Lehmann
6-Amino-1-benzyl-4-(4-chlorophenyl)-3-(4-pyridyl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
Acta Crystallographica Section E
author_facet Stefan Laufer
Dieter Schollmeyer
Frank Lehmann
author_sort Stefan Laufer
title 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_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_sort 6-amino-1-benzyl-4-(4-chlorophenyl)-3-(4-pyridyl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
publisher International Union of Crystallography
series Acta Crystallographica Section E
issn 1600-5368
publishDate 2008-04-01
description The crystal structure of the title compound, C25H18ClN5O, 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)°.
url http://scripts.iucr.org/cgi-bin/paper?S160053680800487X
work_keys_str_mv AT stefanlaufer 6amino1benzyl44chlorophenyl34pyridyl14dihydropyrano23cpyrazole5carbonitrile
AT dieterschollmeyer 6amino1benzyl44chlorophenyl34pyridyl14dihydropyrano23cpyrazole5carbonitrile
AT franklehmann 6amino1benzyl44chlorophenyl34pyridyl14dihydropyrano23cpyrazole5carbonitrile
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