Exploration of SAR features by modifications of thiazoleacetic acids as CRTH2 antagonists

Marie Grimstrup, Jean-Marie Receveur, Øystein Rist, Thomas Frimurer, Peter Aadal Nielsen, Jesper M. Mathiesen, Thomas Högberg

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

Resumé

The SAR features have been further explored for (2-benzhydryl-4-phenyl-thiazol-5-yl)acetic acids as CRTH2 (chemoattractant receptor-homologous molecule expressed on Th2 cells) antagonists. The introduction of a nitrogen or a methyl substituent in the benzhydrylic position offer two alternative drugable scaffolds attractive for unsymmetrically substituted derivatives. An imidazole analogue lacks activity due to formation of a favored coplanar intramolecular hydrogen bond. The pyrimidine derivative 18 represents a potent and selective compound that will be subject to continued investigations.
OriginalsprogEngelsk
TidsskriftBioorganic & Medicinal Chemistry Letters
Vol/bind20
Udgave nummer5
Sider (fra-til)1638-41
ISSN0960-894X
DOI
StatusUdgivet - 2010
Udgivet eksterntJa

Fingeraftryk

Th2 Cells
Hydrogen
Nitrogen
Formyl Peptide Receptor
Derivatives
Acids
Scaffolds
Hydrogen bonds
Acetates
Molecules
pyrimidine
imidazole

Citer dette

Grimstrup, Marie ; Receveur, Jean-Marie ; Rist, Øystein ; Frimurer, Thomas ; Nielsen, Peter Aadal ; Mathiesen, Jesper M. ; Högberg, Thomas. / Exploration of SAR features by modifications of thiazoleacetic acids as CRTH2 antagonists. I: Bioorganic & Medicinal Chemistry Letters. 2010 ; Bind 20, Nr. 5. s. 1638-41.
@article{8a2b80be007842b4a3e2203966f6ff82,
title = "Exploration of SAR features by modifications of thiazoleacetic acids as CRTH2 antagonists",
abstract = "The SAR features have been further explored for (2-benzhydryl-4-phenyl-thiazol-5-yl)acetic acids as CRTH2 (chemoattractant receptor-homologous molecule expressed on Th2 cells) antagonists. The introduction of a nitrogen or a methyl substituent in the benzhydrylic position offer two alternative drugable scaffolds attractive for unsymmetrically substituted derivatives. An imidazole analogue lacks activity due to formation of a favored coplanar intramolecular hydrogen bond. The pyrimidine derivative 18 represents a potent and selective compound that will be subject to continued investigations.",
author = "Marie Grimstrup and Jean-Marie Receveur and {\O}ystein Rist and Thomas Frimurer and Nielsen, {Peter Aadal} and Mathiesen, {Jesper M.} and Thomas H{\"o}gberg",
note = "Copyright 2010 Elsevier Ltd. All rights reserved.",
year = "2010",
doi = "10.1016/j.bmcl.2010.01.092",
language = "English",
volume = "20",
pages = "1638--41",
journal = "Bioorganic & Medicinal Chemistry Letters",
issn = "0960-894X",
publisher = "Pergamon Press",
number = "5",

}

Exploration of SAR features by modifications of thiazoleacetic acids as CRTH2 antagonists. / Grimstrup, Marie; Receveur, Jean-Marie; Rist, Øystein; Frimurer, Thomas; Nielsen, Peter Aadal; Mathiesen, Jesper M.; Högberg, Thomas.

I: Bioorganic & Medicinal Chemistry Letters, Bind 20, Nr. 5, 2010, s. 1638-41.

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

TY - JOUR

T1 - Exploration of SAR features by modifications of thiazoleacetic acids as CRTH2 antagonists

AU - Grimstrup, Marie

AU - Receveur, Jean-Marie

AU - Rist, Øystein

AU - Frimurer, Thomas

AU - Nielsen, Peter Aadal

AU - Mathiesen, Jesper M.

AU - Högberg, Thomas

N1 - Copyright 2010 Elsevier Ltd. All rights reserved.

PY - 2010

Y1 - 2010

N2 - The SAR features have been further explored for (2-benzhydryl-4-phenyl-thiazol-5-yl)acetic acids as CRTH2 (chemoattractant receptor-homologous molecule expressed on Th2 cells) antagonists. The introduction of a nitrogen or a methyl substituent in the benzhydrylic position offer two alternative drugable scaffolds attractive for unsymmetrically substituted derivatives. An imidazole analogue lacks activity due to formation of a favored coplanar intramolecular hydrogen bond. The pyrimidine derivative 18 represents a potent and selective compound that will be subject to continued investigations.

AB - The SAR features have been further explored for (2-benzhydryl-4-phenyl-thiazol-5-yl)acetic acids as CRTH2 (chemoattractant receptor-homologous molecule expressed on Th2 cells) antagonists. The introduction of a nitrogen or a methyl substituent in the benzhydrylic position offer two alternative drugable scaffolds attractive for unsymmetrically substituted derivatives. An imidazole analogue lacks activity due to formation of a favored coplanar intramolecular hydrogen bond. The pyrimidine derivative 18 represents a potent and selective compound that will be subject to continued investigations.

U2 - 10.1016/j.bmcl.2010.01.092

DO - 10.1016/j.bmcl.2010.01.092

M3 - Journal article

C2 - 20137942

VL - 20

SP - 1638

EP - 1641

JO - Bioorganic & Medicinal Chemistry Letters

JF - Bioorganic & Medicinal Chemistry Letters

SN - 0960-894X

IS - 5

ER -