volume 60 issue 17 pages 7524-7538

5-(4,6-Dimorpholino-1,3,5-triazin-2-yl)-4-(trifluoromethyl)pyridin-2-amine (PQR309), a Potent, Brain-Penetrant, Orally Bioavailable, Pan-Class I PI3K/mTOR Inhibitor as Clinical Candidate in Oncology

Florent Beaufils 1
Natasa Cmiljanovic 1
Vladimir Cmiljanovic 1
Thomas Bohnacker 1
Anna Melone 1
Romina Marone 1
Eileen Jackson 1
Xuxiao Zhang 2
Alexander M Sele 1
Chiara Borsari 1
Jürgen Mestan 3
Paul Hebeisen 3
Petra Hillmann 3
Bernd Giese 4
Marketa Zvelebil 1
Doriano Fabbro 3
Roger L Williams 2
Denise Rageot 1
Matthias Wymann 1
2
 
MRC Laboratory of Molecular Biology, Francis Crick Avenue, Cambridge CB2 0QH, U.K.
3
 
PIQUR Therapeutics AG, Hochbergerstrasse 60C, 4057 Basel, Switzerland
Publication typeJournal Article
Publication date2017-09-01
scimago Q1
wos Q1
SJR1.801
CiteScore11.5
Impact factor6.8
ISSN00222623, 15204804
Drug Discovery
Molecular Medicine
Abstract
Phosphoinositide 3-kinase (PI3K) is deregulated in a wide variety of human tumors and triggers activation of protein kinase B (PKB/Akt) and mammalian target of rapamycin (mTOR). Here we describe the preclinical characterization of compound 1 (PQR309, bimiralisib), a potent 4,6-dimorpholino-1,3,5-triazine-based pan-class I PI3K inhibitor, which targets mTOR kinase in a balanced fashion at higher concentrations. No off-target interactions were detected for 1 in a wide panel of protein kinase, enzyme, and receptor ligand assays. Moreover, 1 did not bind tubulin, which was observed for the structurally related 4 (BKM120, buparlisib). Compound 1 is orally available, crosses the blood-brain barrier, and displayed favorable pharmacokinetic parameters in mice, rats, and dogs. Compound 1 demonstrated efficiency in inhibiting proliferation in tumor cell lines and a rat xenograft model. This, together with the compound's safety profile, identifies 1 as a clinical candidate with a broad application range in oncology, including treatment of brain tumors or CNS metastasis. Compound 1 is currently in phase II clinical trials for advanced solid tumors and refractory lymphoma.
Found 
Found 

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GOST Copy
Beaufils F. et al. 5-(4,6-Dimorpholino-1,3,5-triazin-2-yl)-4-(trifluoromethyl)pyridin-2-amine (PQR309), a Potent, Brain-Penetrant, Orally Bioavailable, Pan-Class I PI3K/mTOR Inhibitor as Clinical Candidate in Oncology // Journal of Medicinal Chemistry. 2017. Vol. 60. No. 17. pp. 7524-7538.
GOST all authors (up to 50) Copy
Beaufils F., Cmiljanovic N., Cmiljanovic V., Bohnacker T., Melone A., Marone R., Jackson E., Zhang X., Sele A. M., Borsari C., Mestan J., Hebeisen P., Hillmann P., Giese B., Zvelebil M., Fabbro D., Williams R. L., Rageot D., Wymann M. 5-(4,6-Dimorpholino-1,3,5-triazin-2-yl)-4-(trifluoromethyl)pyridin-2-amine (PQR309), a Potent, Brain-Penetrant, Orally Bioavailable, Pan-Class I PI3K/mTOR Inhibitor as Clinical Candidate in Oncology // Journal of Medicinal Chemistry. 2017. Vol. 60. No. 17. pp. 7524-7538.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1021/acs.jmedchem.7b00930
UR - https://doi.org/10.1021/acs.jmedchem.7b00930
TI - 5-(4,6-Dimorpholino-1,3,5-triazin-2-yl)-4-(trifluoromethyl)pyridin-2-amine (PQR309), a Potent, Brain-Penetrant, Orally Bioavailable, Pan-Class I PI3K/mTOR Inhibitor as Clinical Candidate in Oncology
T2 - Journal of Medicinal Chemistry
AU - Beaufils, Florent
AU - Cmiljanovic, Natasa
AU - Cmiljanovic, Vladimir
AU - Bohnacker, Thomas
AU - Melone, Anna
AU - Marone, Romina
AU - Jackson, Eileen
AU - Zhang, Xuxiao
AU - Sele, Alexander M
AU - Borsari, Chiara
AU - Mestan, Jürgen
AU - Hebeisen, Paul
AU - Hillmann, Petra
AU - Giese, Bernd
AU - Zvelebil, Marketa
AU - Fabbro, Doriano
AU - Williams, Roger L
AU - Rageot, Denise
AU - Wymann, Matthias
PY - 2017
DA - 2017/09/01
PB - American Chemical Society (ACS)
SP - 7524-7538
IS - 17
VL - 60
PMID - 28829592
SN - 0022-2623
SN - 1520-4804
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2017_Beaufils,
author = {Florent Beaufils and Natasa Cmiljanovic and Vladimir Cmiljanovic and Thomas Bohnacker and Anna Melone and Romina Marone and Eileen Jackson and Xuxiao Zhang and Alexander M Sele and Chiara Borsari and Jürgen Mestan and Paul Hebeisen and Petra Hillmann and Bernd Giese and Marketa Zvelebil and Doriano Fabbro and Roger L Williams and Denise Rageot and Matthias Wymann},
title = {5-(4,6-Dimorpholino-1,3,5-triazin-2-yl)-4-(trifluoromethyl)pyridin-2-amine (PQR309), a Potent, Brain-Penetrant, Orally Bioavailable, Pan-Class I PI3K/mTOR Inhibitor as Clinical Candidate in Oncology},
journal = {Journal of Medicinal Chemistry},
year = {2017},
volume = {60},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://doi.org/10.1021/acs.jmedchem.7b00930},
number = {17},
pages = {7524--7538},
doi = {10.1021/acs.jmedchem.7b00930}
}
MLA
Cite this
MLA Copy
Beaufils, Florent, et al. “5-(4,6-Dimorpholino-1,3,5-triazin-2-yl)-4-(trifluoromethyl)pyridin-2-amine (PQR309), a Potent, Brain-Penetrant, Orally Bioavailable, Pan-Class I PI3K/mTOR Inhibitor as Clinical Candidate in Oncology.” Journal of Medicinal Chemistry, vol. 60, no. 17, Sep. 2017, pp. 7524-7538. https://doi.org/10.1021/acs.jmedchem.7b00930.