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Title: Discovery of Potent, Selective, and Brain-Penetrant 1H-Pyrazol-5-yl-1H-pyrrolo[2,3-b]pyridines as Anaplastic Lymphoma Kinase (ALK) Inhibitors

Journal Article · · Journal of Medicinal Chemistry
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Research Organization:
Brookhaven National Lab. (BNL), Upton, NY (United States)
Sponsoring Organization:
~OTHER
DOE Contract Number:
SC0012704
OSTI ID:
1688808
Report Number(s):
BNL-220140-2020-JACI
Journal Information:
Journal of Medicinal Chemistry, Vol. 62, Issue 10
Country of Publication:
United States
Language:
English

References (31)

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Behavioral and Neurochemical Alterations in Mice Deficient in Anaplastic Lymphoma Kinase Suggest Therapeutic Potential for Psychiatric Indications journal May 2007
Molecular characterization of ALK, a receptor tyrosine kinase expressed specifically in the nervous system journal January 1997
Anaplastic Lymphoma Kinase and Leukocyte Tyrosine Kinase: Functions and genetic interactions in learning, memory and adult neurogenesis journal January 2012
Fusion of a Kinase Gene, ALK , to a Nucleolar Protein Gene, NPM , in Non-Hodgkin's Lymphoma journal March 1994
Identification of the transforming EML4–ALK fusion gene in non-small-cell lung cancer journal July 2007
NPM/ALK downregulates p27Kip1 in a PI-3K-dependent manner journal December 2004
Differential effects of X-ALK fusion proteins on proliferation, transformation, and invasion properties of NIH3T3 cells journal June 2004
Cytoreductive antitumor activity of PF-2341066, a novel inhibitor of anaplastic lymphoma kinase and c-Met, in experimental models of anaplastic large-cell lymphoma journal December 2007
An Orally Available Small-Molecule Inhibitor of c-Met, PF-2341066, Exhibits Cytoreductive Antitumor Efficacy through Antiproliferative and Antiangiogenic Mechanisms journal April 2007
Structure Based Drug Design of Crizotinib (PF-02341066), a Potent and Selective Dual Inhibitor of Mesenchymal–Epithelial Transition Factor (c-MET) Kinase and Anaplastic Lymphoma Kinase (ALK) journal September 2011
Synthesis, Structure–Activity Relationships, and in Vivo Efficacy of the Novel Potent and Selective Anaplastic Lymphoma Kinase (ALK) Inhibitor 5-Chloro- N 2-(2-isopropoxy-5-methyl-4-(piperidin-4-yl)phenyl)- N 4-(2-(isopropylsulfonyl)phenyl)pyrimidine-2,4-diamine (LDK378) Currently in Phase 1 and Phase 2 Clinical Trials journal June 2013
Discovery of Brigatinib (AP26113), a Phosphine Oxide-Containing, Potent, Orally Active Inhibitor of Anaplastic Lymphoma Kinase journal May 2016
Design and synthesis of a highly selective, orally active and potent anaplastic lymphoma kinase inhibitor (CH5424802) journal February 2012
Discovery of (10 R )-7-Amino-12-fluoro-2,10,16-trimethyl-15-oxo-10,15,16,17-tetrahydro- 2H -8,4-(metheno)pyrazolo[4,3- h ][2,5,11]-benzoxadiazacyclotetradecine-3-carbonitrile (PF-06463922), a Macrocyclic Inhibitor of Anaplastic Lymphoma Kinase (ALK) and c-ros Oncogene 1 (ROS1) with Preclinical Brain Exposure and Broad-Spectrum Potency against ALK-Resistant Mutations journal December 2013
Trk signaling regulates neural precursor cell proliferation and differentiation during cortical development journal December 2007
Structural approaches to obtain kinase selectivity journal May 2012
Some Comments on the Conformations of Methyl Phenyl Sulfides, Sulfoxides and Sulfones journal February 1981
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How hydrogen bonds impact P-glycoprotein transport and permeability journal November 2012
Quantitative Investigation of the Impact of P-Glycoprotein Inhibition on Drug Transport across Blood-Brain Barrier in Rats journal October 2010
Establishment and Characterization of the Transformants Stably-Expressing MDR1 Derived from Various Animal Species in LLC-PK1 journal June 2006
Design and Synthesis of Pyrrolo[3,2- d ]pyrimidine Human Epidermal Growth Factor Receptor 2 (HER2)/Epidermal Growth Factor Receptor (EGFR) Dual Inhibitors: Exploration of Novel Back-Pocket Binders journal April 2012
A small molecule–kinase interaction map for clinical kinase inhibitors journal February 2005
Molecular replacement with MOLREP journal December 2009
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Refinement of Macromolecular Structures by the Maximum-Likelihood Method journal May 1997
Towards automated crystallographic structure refinement with phenix.refine journal March 2012

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