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 T.
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
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U2 - 10.1107/S1600536814003031
DO - 10.1107/S1600536814003031
M3 - Article
C2 - 24765003
AN - SCOPUS:84897708043
SN - 1600-5368
VL - 70
SP - o297-o298
JO - Acta Crystallographica Section E: Structure Reports Online
JF - Acta Crystallographica Section E: Structure Reports Online
IS - 3
ER -