메뉴 건너뛰기




Volumn 58, Issue 5, 2015, Pages 2417-2430

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

Author keywords

[No Author keywords available]

Indexed keywords

4 [3 [DIFLUORO(3 METHOXYQUINOLIN 6 YL)METHYL] 8 FLUORO[1,2,4]TRIAZOLO[4,3 A]PYRIDIN 6 YL]THIAZOLE; 4 [3 [DIFLUORO(QUINOLIN 6 YL)METHYL] 8 FLUORO[1,2,4]TRIAZOLO[4,3 A]PYRIDIN 6 YL]THIAZOLE; 5 [3 [DIFLUORO(3 METHOXYQUINOLIN 6 YL)METHYL] 8 FLUORO[1,2,4]TRIAZOLO[4,3 A]PYRIDIN 6 YL] 3 METHYLISOXAZOLE; 5 [3 [DIFLUORO(QUINOLIN 6 YL)METHYL] 8 FLUORO[1,2,4]TRIAZOLO[4,3 A]PYRIDIN 6 YL] 2 METHYLTHIAZOLE; 5 [3 [DIFLUORO(QUINOLIN 6 YL)METHYL] 8 FLUORO[1,2,4]TRIAZOLO[4,3 A]PYRIDIN 6 YL] 3 METHYLISOXAZOLE; 5 [8 FLUORO 3 [1 (3 METHOXYQUINOLIN 6 YL)ETHYL][1,2,4]TRIAZOLO[4,3 A]PYRIDIN 6 YL] 3 METHYLISOTHIAZOLE; 5 [8 FLUORO 3 [1 (QUINOLIN 6 YL)ETHYL][1,2,4]TRIAZOLO[4,3 A]PYRIDIN 6 YL] 3 METHYLISOTHIAZOLE; 5 [8 FLUORO 3 [1 FLUORO 1 (3 METHYOXYQUINOLIN 6 YL)ETHYL][1,2,4]TRIAZOLO[4,3 A]PYRIDIN 6 YL] 3 METHYLISOTHIAZOLE; 5 [8 FLUORO 3 [1 FLUORO 1 (3 METHYOXYQUINOLIN 6 YL)ETHYL][1,2,4]TRIAZOLO[4,3 A]PYRIDIN 6 YL] 3 METHYLISOXAZOLE; 5 [8 FLUORO 3 [1 FLUORO 1 (QUINOLIN 6 YL)ETHYL][1,2,4]TRIAZOLO[4,3 A]PYRIDIN 6 YL] 3 METHYLISOTHIAZOLE; 6 [1 FLUORO 1 [8 FLUORO 6 (1 METHYL 1H PYRAQZOL 4 YL)[1,2,4]TRIAZOLO[4,3 A]PYRIDIN 3 YL]ETHYL] 3 METHOXYQUINOLINE; 6 [1 [8 FLUORO 6 (1 METHYL 1H PYRAZOL 4 YL)[1,2,4]TRIAZOLO[4,3 A]PYRIDIN 3 YL]ETHYL] 3 METHOXYQUINOLINE; 6 [DIFLUORO[8 FLUORO 6 ( 1 METHYL 1H PYRAZOL 4 YL)[1,2,4]TRIAZOLO[4,3 A]PYRIDIN 3 YL]METHYL] 3 METHOXYQUINOLINE; 6 [DIFLUORO[8 FLUORO 6 (1 METHYL 1H PYRAZOL 4 YL)[1,2,4]TRIAZOLO[4,3 A]PYRIDIN 3 YL]METHYL]QUINOLINE; 6 [DIFLUORO[8 FLUORO 6 (PYRIDIN 2 YL)[1,2,4]TRIAZOLO[4,3 A] PYRIDIN 3 YL]METHYL]QUINOLINE; 6 [[8 FLUORO 6 (1 METHYL 1H PYRAZOL 4 YL)[1,2,4]TRIAZOLO[4,3 A]PYRIDIN 3 YL]METHYL] 3 METHOXYQUINOLINE; 6 [[8 FLUORO 6 (1 METHYL 1H PYRAZOL 4 YL)[1,2,4]TRIAZOLO[4,3 A]PYRIDIN 3 YL]METHYL]BENZO[D]THIAZOL 2 AMINE; 6 [[8 FLUORO 6 (1 METHYL 1H PYRAZOL 4 YL)[1,2,4]TRIAZOLO[4,3 A]PYRIDIN 3 YL]METHYL]QUINOLIN 3 OL; 6 [[8 FLUORO 6 (1 METHYL 1H PYRAZOL 4 YL)[1,2,4]TRIAZOLO[4,3 A]PYRIDIN 3 YL]METHYL]QUINOLINE; 6 [[8 FLUORO 6 (1 METHYL 1H PYRAZOL 4 YL)[1,2,4]TRIAZOLO[4,3 A]PYRIDIN 3 YL]METHYL]QUINOXALINE; 8 FLUOROTRIAZOLOPYRIDINE; CYTOCHROME P450 2D6; CYTOCHROME P450 3A4; GLUTATHIONE; GLUTATHIONE TRANSFERASE; N [6 [[8 FLUORO 6 (1 METHYL 1H PYRAZOL 4 YL)[1,2,4]TRIAZOLO[4,3 A]PYRIDIN 3 YL]METHYL]BENZO[D]THIAZOL 2 YL]ACETAMIDE; PROTEIN INHIBITOR; PYRIDINE DERIVATIVE; SCATTER FACTOR RECEPTOR; UNCLASSIFIED DRUG; UNINDEXED DRUG; 5-(8-FLUORO-3-(1-(3-(2-METHOXYETHOXY)QUINOLIN-6-YL)ETHYL)(1,2,4)TRIAZOLO(4,3-A)PYRIDIN-6-YL)-3-METHYLISOXAZOLE; PROTEIN KINASE INHIBITOR; QUINOLINE DERIVATIVE; SCATTER FACTOR; TRIAZOLE DERIVATIVE;

EID: 84924714675     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/acs.jmedchem.5b00591     Document Type: Erratum
Times cited : (32)

References (22)
  • 4
    • 44449151030 scopus 로고    scopus 로고
    • 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
    • (2008) Nat. Rev. Drug Discovery , vol.7 , pp. 504-516
    • Comoglio, P.M.1    Giordano, S.2    Trusolino, L.3
  • 5
    • 84902449207 scopus 로고    scopus 로고
    • Targeting receptor tyrosine kinase MET in cancer: Small molecule inhibitors and clinical progress
    • Cui, J. J. Targeting receptor tyrosine kinase MET in cancer: small molecule inhibitors and clinical progress J. Med. Chem. 2014, 57, 4427-4453
    • (2014) J. Med. Chem. , vol.57 , pp. 4427-4453
    • Cui, J.J.1
  • 6
    • 76149091189 scopus 로고    scopus 로고
    • Small molecule c-Met kinase inhibitors: A review of recent patents
    • Porter, J. Small molecule c-Met kinase inhibitors: a review of recent patents Expert Opin. Ther. Pat. 2010, 20, 159-177
    • (2010) Expert Opin. Ther. Pat. , vol.20 , pp. 159-177
    • Porter, J.1
  • 10
    • 77950573400 scopus 로고    scopus 로고
    • 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
    • (2010) J. Med. Chem. , vol.53 , pp. 2681-2694
    • Zuccotto, F.1    Ardini, E.2    Casale, E.3    Angiolini, M.4
  • 11
    • 33847312156 scopus 로고    scopus 로고
    • 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
    • (2007) Tetrahedron Lett. , vol.48 , pp. 2237-2240
    • Wang, Y.1    Sarris, K.2    Sauer, D.R.3    Djuric, S.W.4
  • 13
    • 77953509226 scopus 로고    scopus 로고
    • 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.
    • (2010) Lewis Basicity and Affinity Scales: Data and Measurement , pp. 119-135
    • Laurence, C.1    Gal, J.-F.2
  • 14
    • 0029561598 scopus 로고
    • 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
    • (1995) Crit. Rev. Biochem. Mol. Biol. , vol.30 , pp. 445-600
    • Hayes, J.D.1    Pulford, D.J.2
  • 15
    • 77749262361 scopus 로고    scopus 로고
    • Adverse Drug Reactions
    • Uetrecht, J. Springer: New York
    • 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.
    • (2010) Handbook of Experimental Pharmacology , vol.196 , Issue.PART 3 , pp. 369-405
    • Hinson, J.A.1    Roberts, D.W.2    James, L.P.3
  • 16
    • 34250334344 scopus 로고    scopus 로고
    • 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
    • (2007) ARKIVOC , vol.12 , pp. 132-147
    • Roberge, J.Y.1    Yu, G.2    Mikkilineni, A.3    Wu, X.4    Zhu, Y.5    Lawrence, R.M.6    Ewing, W.R.7
  • 17
    • 34848848499 scopus 로고    scopus 로고
    • Fluorine in pharmaceuticals: Looking beyond intuition
    • Müller, K.; Faeh, C.; Diederich, F. Fluorine in pharmaceuticals: looking beyond intuition Science 2007, 317, 1881-1886
    • (2007) Science , vol.317 , pp. 1881-1886
    • Müller, K.1    Faeh, C.2    Diederich, F.3
  • 18
    • 57449099296 scopus 로고    scopus 로고
    • 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
    • (2008) Chem. Res. Toxicol. , vol.21 , pp. 2216-2222
    • Teffera, Y.1    Colletti, A.E.2    Christophe-Harmange, J.-C.3    Hollis, L.S.4    Albrecht, B.K.5    Boezio, A.A.6    Liu, J.7    Zhao, Z.8
  • 20
    • 46449090520 scopus 로고    scopus 로고
    • 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
    • (2008) Drug Metab. Dispos. , vol.36 , pp. 1267-1274
    • Yamazaki, S.1    Skaptason, J.2    Romero, D.3    Lee, J.H.4    Zou, H.Y.5    Christensen, J.G.6    Koup, J.R.7    Smith, B.J.8    Koudriakova, T.9
  • 21
    • 0034814843 scopus 로고    scopus 로고
    • 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
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 8410-8411
    • Lee, S.1    Beare, N.A.2    Hartwig, J.F.3
  • 22
    • 0032733974 scopus 로고    scopus 로고
    • 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
    • (1999) Drug Metab. Dispos. , vol.27 , pp. 1350-1359
    • Obach, R.S.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.