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

Emmanuel S Akinboye; Ray J Butcher; Sema Ozturk Yildirim; John T Isaacs

doi:10.1107/S1600536814003031

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

Acta Crystallogr Sect E Struct Rep Online. 2014 Feb 15;70(Pt 3):o297-8. doi: 10.1107/S1600536814003031. eCollection 2014 Mar 1.

Authors

Emmanuel S Akinboye¹, Ray J Butcher², Sema Ozturk Yildirim³, John T Isaacs¹

Affiliations

¹ The Sidney Kimmel Comprehensive Cancer Center at Johns Hopkins University, 1650 Orleans Street, Baltimore, MD 21287, USA.
² Department of Chemistry, Howard University, 525 College Street NW, Washington DC 20059, USA.
³ Department of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey.

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.