Abstract
The title compound, C20H17F3N 2O4, 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.
| Original language | English (US) |
|---|---|
| Journal | Acta Crystallographica Section E: Structure Reports Online |
| Volume | 70 |
| Issue number | 3 |
| DOIs | |
| State | Published - Mar 2014 |
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Keywords
- Data-to-parameter ratio = 13.2
- Meanσ(C-C) = 0.002 Å
- R factor = 0.044
- Single-crystal X-ray study
- T = 298 K
- wR factor = 0.132
ASJC Scopus subject areas
- Condensed Matter Physics
- Materials Science(all)
- Chemistry(all)
Cite this
4-Hydroxy-5-methoxy-N,1-dimethyl-2-oxo-N-[4-(trifluoromethyl)phenyl]-1, 2-dihydroquinoline-3-carboxamide. / Akinboye, Emmanuel; Butcher, Ray J.; Yildirim, Sema Ozturk; Isaacs, John Tod.
In: Acta Crystallographica Section E: Structure Reports Online, Vol. 70, No. 3, 03.2014.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - 4-Hydroxy-5-methoxy-N,1-dimethyl-2-oxo-N-[4-(trifluoromethyl)phenyl]-1, 2-dihydroquinoline-3-carboxamide
AU - Akinboye, Emmanuel
AU - Butcher, Ray J.
AU - Yildirim, Sema Ozturk
AU - Isaacs, John Tod
PY - 2014/3
Y1 - 2014/3
N2 - The title compound, C20H17F3N 2O4, 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.
AB - The title compound, C20H17F3N 2O4, 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.
KW - Data-to-parameter ratio = 13.2
KW - Meanσ(C-C) = 0.002 Å
KW - R factor = 0.044
KW - Single-crystal X-ray study
KW - T = 298 K
KW - wR factor = 0.132
UR - http://www.scopus.com/inward/record.url?scp=84897708043&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84897708043&partnerID=8YFLogxK
U2 - 10.1107/S1600536814003031
DO - 10.1107/S1600536814003031
M3 - Article
C2 - 24765003
AN - SCOPUS:84897708043
VL - 70
JO - Acta Crystallographica Section E: Structure Reports Online
JF - Acta Crystallographica Section E: Structure Reports Online
SN - 1600-5368
IS - 3
ER -