Abstract |
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.
|
Authors | Emmanuel S Akinboye, Ray J Butcher, Sema Ozturk Yildirim, John T Isaacs |
Journal | Acta crystallographica. Section E, Structure reports online
(Acta Crystallogr Sect E Struct Rep Online)
Vol. 70
Issue Pt 3
Pg. o297-8
(Mar 01 2014)
ISSN: 1600-5368 [Print] United States |
PMID | 24765003
(Publication Type: Journal Article)
|