4-Hy-droxy-5-meth-oxy-N,1-dimethyl-2-oxo-N-[4-(tri-fluoro-meth-yl)phen-yl]-1,2-di-hydro-quinoline-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 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-(tri-fluoro-meth-yl)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-hy-droxy H atom acts as a double proton donor in an intra-molecular hydrogen bond to the 5-position meth-oxy O atom and in an inter-molecular contact to the 2-oxo group, generating a chain along [010] in the crystal structure.
The Sidney Kimmel Comprehensive Cancer Center at Johns Hopkins University, 1650 Orleans Street, Baltimore, MD 21287, USA.
Emmanuel S
ES
Akinboye
Department of Chemistry, Howard University, 525 College Street NW, Washington DC 20059, USA.
Ray J
RJ
Butcher
Department of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey.
Sema Ozturk
SO
Yildirim
The Sidney Kimmel Comprehensive Cancer Center at Johns Hopkins University, 1650 Orleans Street, Baltimore, MD 21287, USA.
John T
JT
Isaacs