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 Tod Isaacs

Research output: Contribution to journalArticle

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.

Original languageEnglish (US)
JournalActa Crystallographica Section E: Structure Reports Online
Volume70
Issue number3
DOIs
StatePublished - Mar 2014

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quinoline
Atoms
atoms
Conformations
Protons
Hydrogen bonds
Crystal structure
Hydrogen
cancer
analogs
hydrogen bonds
deviation
crystal structure
protons
tasquinimod
rings

Keywords

  • 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

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

Cite this

@article{6ca13ed6727f439093c64104931c089a,
title = "4-Hydroxy-5-methoxy-N,1-dimethyl-2-oxo-N-[4-(trifluoromethyl)phenyl]-1, 2-dihydroquinoline-3-carboxamide",
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 {\AA}). 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.",
keywords = "Data-to-parameter ratio = 13.2, Meanσ(C-C) = 0.002 {\AA}, R factor = 0.044, Single-crystal X-ray study, T = 298 K, wR factor = 0.132",
author = "Emmanuel Akinboye and Butcher, {Ray J.} and Yildirim, {Sema Ozturk} and Isaacs, {John Tod}",
year = "2014",
month = "3",
doi = "10.1107/S1600536814003031",
language = "English (US)",
volume = "70",
journal = "Acta Crystallographica Section E: Structure Reports Online",
issn = "1600-5368",
publisher = "International Union of Crystallography",
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TY - JOUR

T1 - 4-Hydroxy-5-methoxy-N,1-dimethyl-2-oxo-N-[4-(trifluoromethyl)phenyl]-1, 2-dihydroquinoline-3-carboxamide

AU - Akinboye, Emmanuel

AU - Butcher, Ray J.

AU - Yildirim, Sema Ozturk

AU - Isaacs, John Tod

PY - 2014/3

Y1 - 2014/3

N2 - 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.

AB - 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.

KW - Data-to-parameter ratio = 13.2

KW - Meanσ(C-C) = 0.002 Å

KW - R factor = 0.044

KW - Single-crystal X-ray study

KW - T = 298 K

KW - wR factor = 0.132

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M3 - Article

VL - 70

JO - Acta Crystallographica Section E: Structure Reports Online

JF - Acta Crystallographica Section E: Structure Reports Online

SN - 1600-5368

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