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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Format: | Article |
Language: | English |
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International Union of Crystallography
2014-03-01
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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. |
first_indexed | 2024-12-20T11:17:51Z |
format | Article |
id | doaj.art-455e48604a0e47b3a3f95e6309b3ec30 |
institution | Directory Open Access Journal |
issn | 1600-5368 |
language | English |
last_indexed | 2024-12-20T11:17:51Z |
publishDate | 2014-03-01 |
publisher | International Union of Crystallography |
record_format | Article |
series | Acta Crystallographica Section E |
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 |