4-Hydroxy-5-methoxy-N,1-dimethyl-2-oxo-N-[4-(trifluoromethyl)phenyl]-1, 2-dihydroquinoline-3-carboxamide

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Akinboye E. S., Butcher R. J., YILDIRIM S., Isaacs J. T.

Acta Crystallographica Section E: Structure Reports Online, vol.70, no.3, 2014 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 70 Issue: 3
  • Publication Date: 2014
  • Doi Number: 10.1107/s1600536814003031
  • Journal Name: Acta Crystallographica Section E: Structure Reports Online
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Aerospace Database, Communication Abstracts, Metadex, Directory of Open Access Journals, Civil Engineering Abstracts
  • Erciyes University Affiliated: Yes

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.