Corrections to pyridoimidazolones as novel potent inhibitors of v-raf murine sarcoma viral oncogene homologue B1 (BRAF) (Journal of Medicinal Chemistry (2009) 52, (2255-2256) DOI: 10.1021/jm801509w);Pyridoimidazolones as novel potent inhibitors of v-Raf murine sarcoma viral oncogene homologue B1 (BRAF)

Journal of Medicinal Chemistry

Volumn 52, Issue 8, 2009, Pages 2255-2264

  Niculescu Duvaz, Dan ^a   Gaulon, Catherine ^a   Dijkstra, Harmen P ^a   Niculescu Duvaz, Ion ^a   Zambon, Alfonso ^a   Menard, Delphine ^a   Suijkerbuijk, Bart M J M ^a   Nourry, Arnaud ^a   Davies, Lawrence ^a   Manne, Helen ^a   Friedlos, Frank ^a   Ogilvie, Lesley ^a   Hedley, Douglas ^a   Whittaker, Steven ^a   Kirk, Ruth ^a   Gill, Adrian ^b   Taylor, Richard D ^b   Raynaud, Florence I ^a   Moreno Farre, Javier ^a   Marais, Richard ^a   Springer, Caroline J ^a   more..

^a INSTITUTE OF CANCER RESEARCH   (United Kingdom)

^b ASTEX PHARMACEUTICALS   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1 (4 CHLOROPHENYL) 3 [4 (2 OXO 2,3 DIHYDRO 1H IMIDAZO[4,5 B]PYRIDIN 7 YLOXY)PHENYL]UREA; 1 [3 CHLORO 5 (TRIFLUOROMETHYL)PHENYL] 3 [4 (2 OXO 2,3 DIHYDRO 1H IMIDAZO[4,5 B]PYRIDIN 7 YLOXY)PHENYL]UREA; 1 [4 (2,3 DIHYDRO 2 OXO 1H IMIDAZO[4,5 B]PYRIDIN 7 YLOXY)PHENYL] 3 PHENYLUREA; 1 [4 (2,3 DIHYDRO 2 OXO 1H IMIDAZO[4,5 B]PYRIDIN 7 YLOXY)PHENYL] 3 [4 CHLORO 3 (TRIFLUOROMETHYL)PHENYL]UREA; B RAF KINASE; N [4 (2 OXO 2,3 DIHYDRO 1H IMIDAZO[4,5 B]PYRIDIN 7 YLOXY)PHENYL] 3 (TRIFLUOROMETHOXY)BENZAMIDE; N [4 (2 OXO 2,3 DIHYDRO 1H IMIDAZO[4,5 B]PYRIDIN 7 YLOXY)PHENYL] 3 (TRIFLUOROMETHYL) 4 CHOROBENZENESULFONAMIDE; N [4 (2 OXO 2,3 DIHYDRO 1H IMIDAZO[4,5 B]PYRIDIN 7 YLOXY)PHENYL]BENZAMIDE; PROTEIN SERINE THREONINE KINASE INHIBITOR; PYRIDOIMIDAZOLONE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; AREA UNDER THE CURVE; ARTICLE; CANCER CELL CULTURE; CANCER INHIBITION; DRUG CLEARANCE; DRUG DESIGN; DRUG HALF LIFE; DRUG METABOLISM; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ASSAY; ENZYME INHIBITION; FEMALE; HINGE REGION; HUMAN; HUMAN CELL; IC 50; LIVER MICROSOME; MAXIMUM PLASMA CONCENTRATION; MELANOMA CELL; METHYLATION; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION; TECHNIQUE;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; FEMALE; HUMANS; IMIDAZOLES; MELANOMA, EXPERIMENTAL; MICE; MICE, NUDE; MICROSOMES, LIVER; MUTATION; NEOPLASM TRANSPLANTATION; PROTO-ONCOGENE PROTEINS B-RAF; PYRIDINES; STRUCTURE-ACTIVITY RELATIONSHIP; TRANSPLANTATION, HETEROLOGOUS;

EID: 65249087812     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm901076g     Document Type: Erratum

References (24)

1. Wellbrock, C.; Karasarides, M.; Marais, R. The RAF proteins take center stage. Nat. ReV. Mol. Cell Biol. 2004, 5, 875-885.
2. Chiloeches, A.; Marais, R. Mitogen-activated protein kinase cascades as therapeutic targets in cancer. In Targets for Cancer Chemotherapy: Transcription Factors and Other Nuclear Proteins; Humana Press Inc.: Totowa, NJ, 2002; pp 179-206.
3. Kolch, W. Meaningful relationships: the regulation of the Ras/Raf /MEK/ERK pathway by protein interactions. Biochem J. 2000, 351, 289-305.
4. Davies, H.; Bignell, G. R.; Cox, C; Stephen, P.; et al. Mutation of the BRAF gene in human cancers. Nature 2002, 417, 949-954.
5. Tuveson, D. A.; Weber, B. L.; Herlyn, M. BRAF as a potential therapeutic target in melanoma and other malignancies. Cancer Cell 2003, 4, 95-98.
6. Garnett, M. J.; Marais, R. Guilty as charged: B-RAF is a human oncogene. Cancer Cell 2004, 6, 313-319.
7. Wellbrock, C.; Ogilvie, L.; Hedley, D.; Karasarides, M.; Martin, J.; Niculescu-Duvaz, D.; Springer, C. J.; Marais, R. V599EB-RAF is an oncogene in melanocytes. Cancer Res. 2004, 64, 2338-2342.
8. Ikenoue, T.; Hikiba, Y.; Kanai, F.; Tanaka, Y.; Imamura, J.; Imamura, T.; Ohta, M.; Ijichi, H.; Tateishi, K.; Kawakami, T.; Aragaki, J.; Matsumura, M.; Kawabe, T.; Omata, M. Functional analysis of mutations within the kinase activation segment of B-Raf in human colorectal tumors. Cancer Res. 2003, 63, 8132-8137.
9. Karasarides, M.; Chiloeches, A.; Hayward, R.; Niculescu-Duvaz, D.; Scanlon, I.; Friedlos, F.; Ogilvie, L.; Hedley, D.; Martin, J.; Marshall, C. J.; Springer, C. J.; Marais, R. B-RAF is a therapeutic target in melanoma. Oncogene 2004, 23, 6292-6298.
10. Hingorani, S. R.; Jacobetz, M. A.; Robertson, G. P.; Herlyn, M.; Tuveson, D. A. Suppression of BRAF (V599E) in human melanoma abrogates transformation. Cancer Res. 2003, 63, 5198-5202.
11. www.clinicaltrials.gov. NCT00405587: Safety Study of PLX4032 in Patients With Solid Tumors.
12. www.clinicaltrials.gov. NCT00304525: A Study to Evaluate RAF265, an Oral Drug Administered to Subjects With Locally Advanced or Metastatic Melanoma.
13. www.clinicaltrials.gov. NCT00451880: Study of XL281 in Adults With Solid Tumors.
14. Ahmad, T.; Eisen, T. Kinase inhibition with BAY 43-9006 in renal cell carcinoma. Clin. Cancer Res. 2004, 10, 6388S-6392S.
15. Eisen, T.; Ahmad, T.; Flaherty, K. T.; Gore, M.; Kaye, S.; Marais, R.; Gibbens, I.; Hackett, S.; James, M.; Schuchter, L. M; Nathanson, K. L.; Xia, C; Simantov, R.; Schwartz, B.; Poulin-Costello, M.; O'Dwyer, P. J.; Ratain, M. J. Sorafenib in advanced melanoma: a Phase II randomised discontinuation trial analysis. Br. J. Cancer 2006, 95, 581-586.
16. Collins, I.; Workman, P. Design and development of signal transduction inhibitors for cancer treatment: Experience and challenges with kinase targets. Curr Signal Transduction Ther 2006, 1, 13-23.
17. Veber, D. F.; Johnson, S. R.; Cheng, H.-Y.; Smith, B. R.; Ward, K. W.; Kopple, K. D. Molecular Properties That Influence the Oral Bioavailability of Drug Candidates. J. Med. Chem. 2002, 45, 2615-2623.
18. Liao, J. J.-L. Molecular Recognition of Protein Kinase Binding Pockets for Design of Potent and Selective Kinase Inhibitors. J. Med. Chem. 2007, 50, 409-424.
19. Wan, P. T. C; Garnett, M. J.; Roe, S. M.; Lee, S.; Niculescu-Duvaz, D.; Good, V. M.; Project, C. G.; Jones, C. M.; Marshall, C. J.; Springer, C. J.; Barford, D.; Marais, R. Mechanism of activation of the RAF- ERK signaling pathway by oncogenic mutations of B-RAF. Cell 2004, 116, 855-867.
20. Niculescu-Duvaz, I.; Roman, E.; Whittaker, S. R.; Friedlos, F.; Kirk, R.; Scanlon, I. J.; Davies, L. C.; Niculescu-Duvaz, D.; Marais, R.; Springer, C. J. Novel Inhibitors of B-RAF Based on a Disubstituted Pyrazine Scaffold. Generation of a Nanomolar Lead. J. Med. Chem. 2006, 49, 407-416.
21. Smith, N. F.; Hayes, A.; Nutley, B. P.; Raynaud, F. I.; Workman, P. Evaluation of the cassette dosing approach for assessing the pharmacokinetics of geldanamycin analogues in mice. Cancer Chemother. Pharmacol. 2004, 54, 475-486.
22. Nutley, B. P.; Raynaud, F. I.; Wilson, S. C.; Fischer, P. M.; Hayes, A.; Goddard, P. M.; McClue, S. J.; Jarman, M.; Lane, D. P.; Workman, P. Metabolism and pharmacokinetics of the cyclin-dependent kinase inhibitor R-roscovitine in the mouse. Mol. CancerTher 2005, 4, 125- 139.
23. Workman, P.; Twentyman, P.; Balkwill, F. United Kingdom Coordinating Committee on Cancer Research guidelines for the welfare of animals in experimental neoplasia, 2nd Ed. Br. J. Cancer 1998, 77, 1-10.
24. Raynaud, F. I.; Whittaker, S. R.; Fischer, P. M.; McClue, S.; Walton, M. I.; Barrie, S. E.; Garrett, M. D.; Rogers, P.; Clarke, S. J.; Kelland, L. R.; Valenti, M.; Brunton, L.; Eccles, S.; Lane, D. P.; Workman, P. In vitro and in vivo pharmacokinetic-pharmacodynamic relationships for the trisubstituted aminopurine cyclin-dependent kinase inhibitors olomoucine, bohemine and CYC202. Clin. Cancer Res. 2005, 11, 4875-4887. DOI: 10.1021/jm800988r