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

Emmanuel Akinboye, Ray J. Butcher, Sema Ozturk Yildirim, John T. Isaacs

Research output: Contribution to journalArticlepeer-review


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.

Original languageEnglish (US)
Pages (from-to)o297-o298
JournalActa Crystallographica Section E: Structure Reports Online
Issue number3
StatePublished - Mar 2014


  • Data-to-parameter ratio = 13.2
  • Meanσ(C-C) = 0.002 Å
  • R factor = 0.044
  • Single-crystal X-ray study
  • T = 298 K
  • wR factor = 0.132

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Science(all)
  • Condensed Matter Physics


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