Erratum: Correction to discovery of potent and selective 8-fluorotriazolopyridine c-Met inhibitors (Journal of Medicinal Chemistry (2015) 58 (2417-2430) DOI: 10.1021/jm501913a);Discovery of potent and selective 8-fluorotriazolopyridine c-met inhibitors
ANIMAL EXPERIMENT;
ARTICLE;
CRYSTALLOGRAPHY;
CYCLIZATION;
DRUG BIOAVAILABILITY;
DRUG DISTRIBUTION;
DRUG HALF LIFE;
DRUG SYNTHESIS;
FLUORINATION;
HUMAN;
HUMAN CELL;
IC50;
INTRINSIC CLEARANCE;
LIVER MICROSOME;
MALE;
NONHUMAN;
PROTEIN PHOSPHORYLATION;
RAT;
STRUCTURE ACTIVITY RELATION;
ANIMAL;
ANTAGONISTS AND INHIBITORS;
CELL PROLIFERATION;
CHEMICAL STRUCTURE;
CHEMISTRY;
DRUG DESIGN;
DRUG DEVELOPMENT;
DRUG EFFECTS;
DRUG SCREENING;
METABOLISM;
MOUSE;
PATHOLOGY;
PHOSPHORYLATION;
PROSTATIC NEOPLASMS;
SIGNAL TRANSDUCTION;
SPRAGUE DAWLEY RAT;
TISSUE DISTRIBUTION;
ANIMALS;
CELL PROLIFERATION;
DRUG DESIGN;
DRUG DISCOVERY;
HEPATOCYTE GROWTH FACTOR;
HUMANS;
MALE;
MICE;
MICROSOMES, LIVER;
MODELS, MOLECULAR;
MOLECULAR STRUCTURE;
PHOSPHORYLATION;
PROSTATIC NEOPLASMS;
PROTEIN KINASE INHIBITORS;
PROTO-ONCOGENE PROTEINS C-MET;
QUINOLINES;
RATS;
RATS, SPRAGUE-DAWLEY;
SIGNAL TRANSDUCTION;
TISSUE DISTRIBUTION;
TRIAZOLES;
XENOGRAFT MODEL ANTITUMOR ASSAYS;
Germline and somatic mutations in the tyrosine kinase domain of the MET proto-oncogene in papillary renal carcinomas
Schmidt, L.; Duh, F. M.; Chen, F.; Kishida, T.; Glenn, G.; Choyke, P.; Scherer, S. W.; Zhuang, Z.; Lubensky, I.; Dean, M.; Allikmets, R.; Chidambaram, A.; Bergerheim, U. R.; Feltis, J. T.; Casadevall, C.; Zamarron, A.; Bernues, M.; Richard, S.; Lips, C. J.; Walther, M. M.; Tsui, L. C.; Geil, L.; Orcutt, M. L.; Stackhouse, T.; Lipan, J.; Slife, L.; Brauch, H.; Decker, J.; Niehans, G.; Hughson, M. D.; Moch, H.; Storkel, S.; Lerman, M. I.; Linehan, W. M.; Zbar, B. Germline and somatic mutations in the tyrosine kinase domain of the MET proto-oncogene in papillary renal carcinomas Nat. Genet. 1997, 16, 68-73
Drug development of MET inhibitors: Targeting oncogene addition and expedience
Comoglio, P. M.; Giordano, S.; Trusolino, L. Drug development of MET inhibitors: targeting oncogene addition and expedience Nat. Rev. Drug Discovery 2008, 7, 504-516
Discovery and optimization of triazolopyridazines as potent and selective inhibitors of the c-Met kinase
Albrecht, B. A.; Harmange, J.-C.; Bauer, D.; Berry, L.; Bode, C.; Boezio, A. A.; Chen, A.; Choquette, D.; Dussault, I.; Fridrich, C.; Hirai, S.; Hoffman, D.; Larrow, J. F.; Kaplan-Lefko, P.; Lin, J.; Lohman, J.; Long, A. M.; Moriguchi, J.; O'Connor, A.; Potashman, M. H.; Reese, M.; Rex, K. R.; Siegmund, A.; Shah, K.; Shimanovich, R.; Springer, S. K.; Teffera, Y.; Yang, Y.; Zhang, Y.; Bellon, S. F. Discovery and optimization of triazolopyridazines as potent and selective inhibitors of the c-Met kinase J. Med. Chem. 2008, 51, 2879-2882
Through the 'gatekeeper door': Exploiting the active kinase conformation
For a review of kinase inhibitor design, see the following
For a review of kinase inhibitor design, see the following: Zuccotto, F.; Ardini, E.; Casale, E.; Angiolini, M. Through the 'gatekeeper door': exploiting the active kinase conformation J. Med. Chem. 2010, 53, 2681-2694
A simple and efficient automatable one step synthesis of triazolopyridines from carboxylic acids
Wang, Y.; Sarris, K.; Sauer, D. R.; Djuric, S. W. A simple and efficient automatable one step synthesis of triazolopyridines from carboxylic acids Tetrahedron Lett. 2007, 48, 2237-2240
Thermodynamic and Spectroscopic Scales of Hydrogen-Bond Basicity and Affinity
Wiley: New York
Laurence, C.; Gal, J.-F. Thermodynamic and Spectroscopic Scales of Hydrogen-Bond Basicity and Affinity. In Lewis Basicity and Affinity Scales: Data and Measurement; Wiley: New York, 2010; pp 119-135.
The glutathione S-transferase supergene family: Regulation of GST∗ and the contribution of the isoenzymes to cancer chemoprotection and drug resistance
Incubation of inhibitors with RLM and glutathione led to displacement of the 8-fluorine even in the absence of NADPH. For a review on GSH conjugation see the following
Incubation of inhibitors with RLM and glutathione led to displacement of the 8-fluorine even in the absence of NADPH. For a review on GSH conjugation see the following: Hayes, J. D.; Pulford, D. J. The glutathione S-transferase supergene family: regulation of GST∗ and the contribution of the isoenzymes to cancer chemoprotection and drug resistance Crit. Rev. Biochem. Mol. Biol. 1995, 30, 445-600
Hinson, J. A.; Roberts, D. W.; James, L. P. Adverse Drug Reactions. In Handbook of Experimental Pharmacology; Uetrecht, J., Ed.; Springer: New York, 2010; Vol. 196, Part 3, pp 369-405.
Synthesis of triazolopyridines and triazolopyrimidines using a modified Mitsunobu reaction
Roberge, J. Y.; Yu, G.; Mikkilineni, A.; Wu, X.; Zhu, Y.; Lawrence, R. M.; Ewing, W. R. Synthesis of triazolopyridines and triazolopyrimidines using a modified Mitsunobu reaction ARKIVOC 2007, 12, 132-147
Chemical reactivity of methoxy 4-O-aryl quinolines: Identification of glutathione displacement products in vitro and in vivo
For a more detailed description of the methods used in these experiments see the following: Teffera, Y.; Colletti, A. E.; Christophe-Harmange, J.-C.; Hollis, L. S.; Albrecht, B. K.; Boezio, A. A.; Liu, J.; Zhao, Z. Chemical reactivity of methoxy 4-O-aryl quinolines: identification of glutathione displacement products in vitro and in vivo Chem. Res. Toxicol. 2008, 21, 2216-2222
For an analysis of electronic properties of various five-membered heterocycles, see the following: Katritzky, A. R.; Pozharskii, A. F. Handbook of Heterocyclic Chemistry, 2 nd ed.; Pergamon: Amsterdam, 2000; p 378.
Pharmacokinetic-pharmacodynamic modeling of biomarker response and tumor growth inhibition to an orally available cMet kinase inhibitor in human tumor xenograft mouse models
For a discussion of the relationship between c-Met target coverage and tumor growth inhibition, see the following: Yamazaki, S.; Skaptason, J.; Romero, D.; Lee, J. H.; Zou, H. Y.; Christensen, J. G.; Koup, J. R.; Smith, B. J.; Koudriakova, T. Pharmacokinetic-pharmacodynamic modeling of biomarker response and tumor growth inhibition to an orally available cMet kinase inhibitor in human tumor xenograft mouse models Drug Metab. Dispos. 2008, 36, 1267-1274
Palladium-catalyzed α-arylation of esters and protected amino acids
Procedure adapted from the following
Procedure adapted from the following: Lee, S.; Beare, N. A.; Hartwig, J. F. Palladium-catalyzed α-arylation of esters and protected amino acids J. Am. Chem. Soc. 2001, 123, 8410-8411
Prediction of human clearance of twenty-nine drugs from hepatic microsomal intrinsic clearance data: An examination of in vitro half-life approach and nonspecific binding to microsomes
Obach, R. S. Prediction of human clearance of twenty-nine drugs from hepatic microsomal intrinsic clearance data: an examination of in vitro half-life approach and nonspecific binding to microsomes Drug Metab. Dispos. 1999, 27, 1350-1359