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

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

doi:10.1107/S1600536814003031

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

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

Research output: Contribution to journal › Article › peer-review

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 language	English (US)
Pages (from-to)	o297-o298
Journal	Acta Crystallographica Section E: Structure Reports Online
Volume	70
Issue number	3
DOIs	https://doi.org/10.1107/S1600536814003031
State	Published - Mar 2014
Externally published	Yes

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

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

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10.1107/S1600536814003031

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@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 = "Akinboye, {Emmanuel S.} and Butcher, {Ray J.} and Yildirim, {Sema Ozturk} and Isaacs, {John T.}",

year = "2014",

month = mar,

doi = "10.1107/S1600536814003031",

language = "English (US)",

volume = "70",

pages = "o297--o298",

journal = "Acta Crystallographica Section E: Structure Reports Online",

issn = "1600-5368",

publisher = "International Union of Crystallography",

number = "3",

}

TY - JOUR

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

AU - Akinboye, Emmanuel S.

AU - Butcher, Ray J.

AU - Yildirim, Sema Ozturk

AU - Isaacs, John T.

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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U2 - 10.1107/S1600536814003031

DO - 10.1107/S1600536814003031

M3 - Article

C2 - 24765003

AN - SCOPUS:84897708043

VL - 70

SP - o297-o298

JO - Acta Crystallographica Section E: Structure Reports Online

JF - Acta Crystallographica Section E: Structure Reports Online

SN - 1600-5368

IS - 3

ER -

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

Abstract

Keywords

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