Journal of Medicinal Chemistry, volume 49, issue 13, pages 3857-3871
Furan-2-ylmethylene Thiazolidinediones as Novel, Potent, and Selective Inhibitors of Phosphoinositide 3-Kinase γ
Vincent Pomel
1
,
Jasna Klicic
1
,
David Covini
1
,
Dennis D Church
1
,
Jeffrey P. Shaw
1
,
Karen Roulin
1
,
Fabienne Burgat Charvillon
1
,
Delphine Valognes
1
,
Montserrat Camps
1
,
Christian Chabert
1
,
Corinne Gillieron
1
,
Bernard Françon
1
,
Dominique Perrin
1
,
Didier Leroy
1
,
Denise Gretener
1
,
Anthony Nichols
1
,
Pierre-Alain Vitte
1
,
Susanna Carboni
1
,
Christian Rommel
1
,
Matthias K. Schwarz
1
,
Thomas Ruckle
1
1
Departments of Chemistry, Signal Transduction, Biochemical Pharmacology, and Experimental Pharmacology, Serono Pharmaceutical Research Institute, 14 Chemin des Aulx, CH-1228 Plan-les-Ouates, Geneva, Switzerland
|
Publication type: Journal Article
Publication date: 2006-06-01
Journal:
Journal of Medicinal Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 7.3
ISSN: 00222623, 15204804
Drug Discovery
Molecular Medicine
Abstract
Class I phosphoinositide 3-kinases (PI3Ks), in particular PI3Kgamma, have become attractive drug targets for inflammatory and autoimmune diseases. Here, we disclose a novel series of furan-2-ylmethylene thiazolidinediones as selective, ATP-competitive PI3Kgamma inhibitors. Structure-based design and X-ray crystallography of complexes formed by inhibitors bound to PI3Kgamma identified key pharmacophore features for potency and selectivity. An acidic NH group on the thiazolidinedione moiety and a hydroxy group on the furan-2-yl-phenyl part of the molecule play crucial roles in binding to PI3K and contribute to class IB PI3K selectivity. Compound 26 (AS-252424), a potent and selective small-molecule PI3Kgamma inhibitor emerging from these efforts, was further profiled in three different cellular PI3K assays and shown to be selective for class IB PI3K-mediated cellular effects. Oral administration of 26 in a mouse model of acute peritonitis led to a significant reduction of leukocyte recruitment.
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Citations by publishers
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- We do not take into account publications without a DOI.
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Pomel V. et al. Furan-2-ylmethylene Thiazolidinediones as Novel, Potent, and Selective Inhibitors of Phosphoinositide 3-Kinase γ // Journal of Medicinal Chemistry. 2006. Vol. 49. No. 13. pp. 3857-3871.
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Pomel V., Klicic J., Covini D., Church D. D., Shaw J. P., Roulin K., Burgat Charvillon F., Valognes D., Camps M., Chabert C., Gillieron C., Françon B., Perrin D., Leroy D., Gretener D., Nichols A., Vitte P., Carboni S., Rommel C., Schwarz M. K., Ruckle T. Furan-2-ylmethylene Thiazolidinediones as Novel, Potent, and Selective Inhibitors of Phosphoinositide 3-Kinase γ // Journal of Medicinal Chemistry. 2006. Vol. 49. No. 13. pp. 3857-3871.
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TY - JOUR
DO - 10.1021/jm0601598
UR - https://doi.org/10.1021/jm0601598
TI - Furan-2-ylmethylene Thiazolidinediones as Novel, Potent, and Selective Inhibitors of Phosphoinositide 3-Kinase γ
T2 - Journal of Medicinal Chemistry
AU - Pomel, Vincent
AU - Klicic, Jasna
AU - Covini, David
AU - Church, Dennis D
AU - Shaw, Jeffrey P.
AU - Roulin, Karen
AU - Burgat Charvillon, Fabienne
AU - Valognes, Delphine
AU - Camps, Montserrat
AU - Chabert, Christian
AU - Gillieron, Corinne
AU - Françon, Bernard
AU - Perrin, Dominique
AU - Leroy, Didier
AU - Gretener, Denise
AU - Nichols, Anthony
AU - Vitte, Pierre-Alain
AU - Carboni, Susanna
AU - Rommel, Christian
AU - Schwarz, Matthias K.
AU - Ruckle, Thomas
PY - 2006
DA - 2006/06/01 00:00:00
PB - American Chemical Society (ACS)
SP - 3857-3871
IS - 13
VL - 49
SN - 0022-2623
SN - 1520-4804
ER -
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@article{2006_Pomel,
author = {Vincent Pomel and Jasna Klicic and David Covini and Dennis D Church and Jeffrey P. Shaw and Karen Roulin and Fabienne Burgat Charvillon and Delphine Valognes and Montserrat Camps and Christian Chabert and Corinne Gillieron and Bernard Françon and Dominique Perrin and Didier Leroy and Denise Gretener and Anthony Nichols and Pierre-Alain Vitte and Susanna Carboni and Christian Rommel and Matthias K. Schwarz and Thomas Ruckle},
title = {Furan-2-ylmethylene Thiazolidinediones as Novel, Potent, and Selective Inhibitors of Phosphoinositide 3-Kinase γ},
journal = {Journal of Medicinal Chemistry},
year = {2006},
volume = {49},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/jm0601598},
number = {13},
pages = {3857--3871},
doi = {10.1021/jm0601598}
}
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Pomel, Vincent, et al. “Furan-2-ylmethylene Thiazolidinediones as Novel, Potent, and Selective Inhibitors of Phosphoinositide 3-Kinase γ.” Journal of Medicinal Chemistry, vol. 49, no. 13, Jun. 2006, pp. 3857-3871. https://doi.org/10.1021/jm0601598.