4-Hydroxy-5-methoxy-N,1-dimethyl-2-oxo-N-[4-(trifluoromethyl)phenyl]-1,2-dihydroquinoline-3-carboxamide

The title compound, C20H17F3N2O4, named tasquinimod, is a second-generation oral quinoline-3-carboxamide analogue, which is currently in phase III clinical trials for the treatment of metastatic prostate cancer. The quinoline unit is almost planar (r.m.s. deviation of fitted atoms = 0.0075 Å). The c...

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Main Authors: Emmanuel S. Akinboye, Ray J. Butcher, Sema Ozturk Yildirim, John T. Isaacs
Format: Article
Language:English
Published: International Union of Crystallography 2014-03-01
Series:Acta Crystallographica Section E
Online Access:http://scripts.iucr.org/cgi-bin/paper?S1600536814003031
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author Emmanuel S. Akinboye
Ray J. Butcher
Sema Ozturk Yildirim
John T. Isaacs
author_facet Emmanuel S. Akinboye
Ray J. Butcher
Sema Ozturk Yildirim
John T. Isaacs
author_sort Emmanuel S. Akinboye
collection DOAJ
description The title compound, C20H17F3N2O4, named tasquinimod, is a second-generation oral quinoline-3-carboxamide analogue, which is currently in phase III clinical trials for the treatment of metastatic prostate cancer. The quinoline unit is almost planar (r.m.s. deviation of fitted atoms = 0.0075 Å). The carboxamide side chain, substituted at position 3, is tilted by 88.07 (7)° to the quinoline plane. Both the methyl and carbonyl groups of this carboxamide side chain are in a syn conformation. The 4-(trifluoromethyl)phenyl plane is inclined at 50.62 (17)° to the plane of the carboxamide side chain, and at 87.14 (4)° to the plane of the quinoline ring system. The 4-hydroxy H atom acts as a double proton donor in an intramolecular hydrogen bond to the 5-position methoxy O atom and in an intermolecular contact to the 2-oxo group, generating a chain along [010] in the crystal structure.
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spelling doaj.art-455e48604a0e47b3a3f95e6309b3ec302022-12-21T19:42:34ZengInternational Union of CrystallographyActa Crystallographica Section E1600-53682014-03-01703o297o29810.1107/S1600536814003031kp24644-Hydroxy-5-methoxy-N,1-dimethyl-2-oxo-N-[4-(trifluoromethyl)phenyl]-1,2-dihydroquinoline-3-carboxamideEmmanuel S. Akinboye0Ray J. Butcher1Sema Ozturk Yildirim2John T. Isaacs3The Sidney Kimmel Comprehensive Cancer Center at Johns Hopkins University, 1650 Orleans Street, Baltimore, MD 21287, USADepartment of Chemistry, Howard University, 525 College Street NW, Washington DC 20059, USADepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, TurkeyThe Sidney Kimmel Comprehensive Cancer Center at Johns Hopkins University, 1650 Orleans Street, Baltimore, MD 21287, USAThe title compound, C20H17F3N2O4, named tasquinimod, is a second-generation oral quinoline-3-carboxamide analogue, which is currently in phase III clinical trials for the treatment of metastatic prostate cancer. The quinoline unit is almost planar (r.m.s. deviation of fitted atoms = 0.0075 Å). The carboxamide side chain, substituted at position 3, is tilted by 88.07 (7)° to the quinoline plane. Both the methyl and carbonyl groups of this carboxamide side chain are in a syn conformation. The 4-(trifluoromethyl)phenyl plane is inclined at 50.62 (17)° to the plane of the carboxamide side chain, and at 87.14 (4)° to the plane of the quinoline ring system. The 4-hydroxy H atom acts as a double proton donor in an intramolecular hydrogen bond to the 5-position methoxy O atom and in an intermolecular contact to the 2-oxo group, generating a chain along [010] in the crystal structure.http://scripts.iucr.org/cgi-bin/paper?S1600536814003031
spellingShingle Emmanuel S. Akinboye
Ray J. Butcher
Sema Ozturk Yildirim
John T. Isaacs
4-Hydroxy-5-methoxy-N,1-dimethyl-2-oxo-N-[4-(trifluoromethyl)phenyl]-1,2-dihydroquinoline-3-carboxamide
Acta Crystallographica Section E
title 4-Hydroxy-5-methoxy-N,1-dimethyl-2-oxo-N-[4-(trifluoromethyl)phenyl]-1,2-dihydroquinoline-3-carboxamide
title_full 4-Hydroxy-5-methoxy-N,1-dimethyl-2-oxo-N-[4-(trifluoromethyl)phenyl]-1,2-dihydroquinoline-3-carboxamide
title_fullStr 4-Hydroxy-5-methoxy-N,1-dimethyl-2-oxo-N-[4-(trifluoromethyl)phenyl]-1,2-dihydroquinoline-3-carboxamide
title_full_unstemmed 4-Hydroxy-5-methoxy-N,1-dimethyl-2-oxo-N-[4-(trifluoromethyl)phenyl]-1,2-dihydroquinoline-3-carboxamide
title_short 4-Hydroxy-5-methoxy-N,1-dimethyl-2-oxo-N-[4-(trifluoromethyl)phenyl]-1,2-dihydroquinoline-3-carboxamide
title_sort 4 hydroxy 5 methoxy n 1 dimethyl 2 oxo n 4 trifluoromethyl phenyl 1 2 dihydroquinoline 3 carboxamide
url http://scripts.iucr.org/cgi-bin/paper?S1600536814003031
work_keys_str_mv AT emmanuelsakinboye 4hydroxy5methoxyn1dimethyl2oxon4trifluoromethylphenyl12dihydroquinoline3carboxamide
AT rayjbutcher 4hydroxy5methoxyn1dimethyl2oxon4trifluoromethylphenyl12dihydroquinoline3carboxamide
AT semaozturkyildirim 4hydroxy5methoxyn1dimethyl2oxon4trifluoromethylphenyl12dihydroquinoline3carboxamide
AT johntisaacs 4hydroxy5methoxyn1dimethyl2oxon4trifluoromethylphenyl12dihydroquinoline3carboxamide