Design, synthesis, and biological evaluation of novel imidazo[1,2-a]pyridine derivatives as potent c-met inhibitors

ACS Medicinal Chemistry Letters

Volumn 6, Issue 5, 2015, Pages 507-512

  Li, Chunpu ^a   Ai, Jing ^a   Zhang, Dengyou ^a   Peng, Xia ^a   Chen, Xi ^a   Gao, Zhiwei ^a   Su, Yi ^a   Zhu, Wei ^a   Ji, Yinchun ^a   Chen, Xiaoyan ^a   Geng, Meiyu ^a   Liu, Hong ^a  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

c Met inhibitor; imidazo 1,2 a pyridine; metabolic stability; Receptor tyrosine kinase

Indexed keywords

AMIDE; ANTINEOPLASTIC AGENT; BENZENE DERIVATIVE; DRUG METABOLITE; IMIDAZO[1,2 A]PYRIDINE DERIVATIVE; SCATTER FACTOR RECEPTOR;

AMINO TERMINAL SEQUENCE; ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; AREA UNDER THE CURVE; ARTICLE; CANCER CELL LINE; CANCER INHIBITION; CELL INVASION; CELL MIGRATION; CELL PROLIFERATION; CELL VIABILITY; DOG; DRUG BIOAVAILABILITY; DRUG DESIGN; DRUG EFFICACY; DRUG SCREENING; DRUG SYNTHESIS; HAPLORHINI; HINGE REGION; HUMAN; HUMAN TISSUE; HYDROGEN BOND; IC50; LIVER MICROSOME; METABOLIC STABILITY; METABOLITE; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROTEIN PHOSPHORYLATION; QUADRUPOLE MASS SPECTROMETRY; RAT; S PHASE CELL CYCLE CHECKPOINT; TIME OF FLIGHT MASS SPECTROMETRY; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY;

EID: 84929327141     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml5004876     Document Type: Article

References (23)

1. Zwick, E.; Bange, J.; Ullrich, A. Receptor tyrosine kinase signalling as a target for cancer intervention strategies Endocr. Relat. Cancer 2001, 8, 161-173
2. Trusolino, L.; Comoglio, P. M. Scatter-factor and semaphorin receptors: cell signalling for invasive growth Nat. Rev. Cancer 2002, 2, 289-300
3. Bottaro, D. P.; Rubin, J. S.; Faletto, D. L.; Chan, A. M.; Kmiecik, T. E.; Vande Woude, G. F.; Aaronson, S. A. Identification of the hepatocyte growth factor receptor as the c-met proto-oncogene product Science 1991, 251, 802-804
4. Garouniatis, A.; Zizi-Sermpetzoglou, A.; Rizos, S.; Kostakis, A.; Nikiteas, N.; Papavassiliou, A. G. Vascular endothelial growth factor receptors 1,3 and caveolin-1 are implicated in colorectal cancer aggressiveness and prognosis - correlations with epidermal growth factor receptor, CD44v6, focal adhesion kinase, and c-Met Tumour Biol. 2013, 34, 2109-2117
5. Porter, J. Small molecule c-Met kinase inhibitors: a review of recent patents Expert Opin. Ther. Pat. 2010, 20, 159-177
6. Parr, C.; Watkins, G.; Mansel, R. E.; Jiang, W. G. The hepatocyte growth factor regulatory factors in human breast cancer Clin. Cancer Res. 2004, 10, 202-211
7. Engelman, J. A.; Zejnullahu, K.; Mitsudomi, T.; Song, Y.; Hyland, C.; Park, J. O.; Lindeman, N.; Gale, C. M.; Zhao, X.; Christensen, J.; Kosaka, T.; Holmes, A. J.; Rogers, A. M.; Cappuzzo, F.; Mok, T.; Lee, C.; Johnson, B. E.; Cantley, L. C.; Janne, P. A. MET amplification leads to gefitinib resistance in lung cancer by activating ERBB3 signaling Science 2007, 316, 1039-1043
8. Cui, J. J.; Tran-Dube, M.; Shen, H.; Nambu, M.; Kung, P. P.; Pairish, M.; Jia, L.; Meng, J.; Funk, L.; Botrous, I.; McTigue, M.; Grodsky, N.; Ryan, K.; Padrique, E.; Alton, G.; Timofeevski, S.; Yamazaki, S.; Li, Q.; Zou, H.; Christensen, J.; Mroczkowski, B.; Bender, S.; Kania, R. S.; Edwards, M. P. 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) J. Med. Chem. 2011, 54, 6342-6363
9. Clinical trial data: https://www.clinicaltrials.gov/ct2/show/NCT00651365.
10. Diamond, S.; Boer, J.; Maduskuie, T. P., Jr.; Falahatpisheh, N.; Li, Y.; Yeleswaram, S. Species-specific metabolism of SGX523 by aldehyde oxidase and the toxicological implications Drug Metab. Dispos. 2010, 38, 1277-1285
11. Cui, J. J.; McTigue, M.; Nambu, M.; Tran-Dube, M.; Pairish, M.; Shen, H.; Jia, L.; Cheng, H.; Hoffman, J.; Le, P.; Jalaie, M.; Goetz, G. H.; Ryan, K.; Grodsky, N.; Deng, Y. L.; Parker, M.; Timofeevski, S.; Murray, B. W.; Yamazaki, S.; Aguirre, S.; Li, Q.; Zou, H.; Christensen, J. Discovery of a novel class of exquisitely selective mesenchymal-epithelial transition factor (c-MET) protein kinase inhibitors and identification of the clinical candidate 2-(4-(1-(quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)-1H-pyrazol-1 -yl)ethanol (PF-04217903) for the treatment of cancer J. Med. Chem. 2012, 55, 8091-8109
12. Clinical trial data: https://www.clinicaltrials.gov/ct2/show/NCT02016534.
13. Clinical trial data: https://www.clinicaltrials.gov/ct2/show/NCT01737827.
14. Clinical trial data: https://www.clinicaltrials.gov/ct2/show/NCT00706355.
15. Humphries, A. C.; Gancia, E.; Gilligan, M. T.; Goodacre, S.; Hallett, D.; Merchant, K. J.; Thomas, S. R. 8-Fluoroimidazo[1,2- a ]pyridine: synthesis, physicochemical properties and evaluation as a bioisosteric replacement for imidazo[1,2- a ]pyrimidine in an allosteric modulator ligand of the GABA A receptor Bioorg. Med. Chem. Lett. 2006, 16, 1518-1522
16. Glide, version 5.5, Schrödinger, LLC, New York, NY, 2009.
17. PyMOL, Version 1.4.1, Schrödinger, LLC, New York, NY, 2011.
18. Bertotti, A.; Burbridge, M. F.; Gastaldi, S.; Galimi, F.; Torti, D.; Medico, E.; Giordano, S.; Corso, S.; Rolland-Valognes, G.; Lockhart, B. P.; Hickman, J. A.; Comoglio, P. M.; Trusolino, L. Only a subset of Met-activated pathways are required to sustain oncogene addiction Sci. Signaling 2009, 2, ra80
19. Jeffers, M.; Rong, S.; Vande Woude, G. F. Hepatocyte growth factor/scatter factor-Met signaling in tumorigenicity and invasion/metastasis J. Mol. Med. 1996, 74, 505-513
20. Stoker, M.; Gherardi, E.; Perryman, M.; Gray, J. Scatter factor is a fibroblast-derived modulator of epithelial cell mobility Nature 1987, 327, 239-242
21. Thiery, J. P. Epithelial-mesenchymal transitions in tumour progression Nat. Rev. Cancer 2002, 2, 442-54
22. Gherardi, E.; Birchmeier, W.; Birchmeier, C.; Vande Woude, G.; Targeting, M. E. T. in cancer: rationale and progress Nat. Rev. Cancer 2012, 12, 89-103
23. Zhou, J.; Metcalf, B.; Xu, M.; He, C.; Zhang, C.; Qian, D.; Burns, D. M.; Li, Y.; Yao, W. Imidazotriazines and Imidazopyrimidines as kinase inhibitors. PCT Int. Appl. WO 2008/064157A1, 2008.