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Discovery of a novel series of quinoxalines as inhibitors of c-Met kinase.

Porter J, Lumb S, Lecomte F, Reuberson J, Foley A, Calmiano M, le Riche K, Edwards H, Delgado J, Franklin RJ, Gascon-Simorte JM, Maloney A, Meier C, Batchelor M
Bioorg Med Chem Lett 19 397-400 (2009)
Cited: 31 times
EuropePMC logo PMID: 19059779

Abstract

A series of quinoxaline inhibitors of c-Met kinase is described. The postulated binding mode was confirmed by an X-ray crystal structure and optimisation of the series was performed on the basis of this structure. Future directions for development of the series are discussed together with the identification of a novel quinoline scaffold.

Articles - 3f66 mentioned but not cited (8)

  1. A novel mechanism by which small molecule inhibitors induce the DFG flip in Aurora A. Martin MP, Zhu JY, Lawrence HR, Pireddu R, Luo Y, Alam R, Ozcan S, Sebti SM, Lawrence NJ, Schönbrunn E. ACS Chem Biol 7 698-706 (2012)
  2. Survey of phosphorylation near drug binding sites in the Protein Data Bank (PDB) and their effects. Smith KP, Gifford KM, Waitzman JS, Rice SE. Proteins 83 25-36 (2015)
  3. BoBER: web interface to the base of bioisosterically exchangeable replacements. Lešnik S, Škrlj B, Eržen N, Bren U, Gobec S, Konc J, Janežič D. J Cheminform 9 62 (2017)
  4. Data driven polypharmacological drug design for lung cancer: analyses for targeting ALK, MET, and EGFR. Narayanan D, Gani OABSM, Gruber FXE, Engh RA. J Cheminform 9 43 (2017)
  5. The dipeptidyl peptidase IV inhibitors vildagliptin and K-579 inhibit a phospholipase C: a case of promiscuous scaffolds in proteins. Chakraborty S, Rendón-Ramírez A, Ásgeirsson B, Dutta M, Ghosh AS, Oda M, Venkatramani R, Rao BJ, Dandekar AM, Goñi FM. F1000Res 2 286 (2013)
  6. Large-Scale Virtual Screening Against the MET Kinase Domain Identifies a New Putative Inhibitor Type. Bresso E, Furlan A, Noel P, Leroux V, Maina F, Dono R, Maigret B. Molecules 25 E938 (2020)
  7. Prediction of kinase-inhibitor binding affinity using energetic parameters. Usha S, Selvaraj S. Bioinformation 12 172-181 (2016)
  8. Preparing a database of corrected protein structures important in cell signaling pathways. Hatami S, Sirous H, Mahnam K, Najafipour A, Fassihi A. Res Pharm Sci 18 67-77 (2023)


Reviews citing this publication (5)

  1. Small molecule c-Met kinase inhibitors: a review of recent patents. Porter J. Expert Opin Ther Pat 20 159-177 (2010)
  2. Quinoxaline-Based Scaffolds Targeting Tyrosine Kinases and Their Potential Anticancer Activity. El Newahie AM, Ismail NS, Abou El Ella DA, Abouzid KA. Arch Pharm (Weinheim) 349 309-326 (2016)
  3. Present status of quinoxaline motifs: excellent pathfinders in therapeutic medicine. Ajani OO. Eur J Med Chem 85 688-715 (2014)
  4. c-MET kinase inhibitors: a patent review (2011 - 2013). Zhu K, Kong X, Zhao D, Liang Z, Luo C. Expert Opin Ther Pat 24 217-230 (2014)
  5. Quinoxaline and quinoxaline-1,4-di-N-oxides: An emerging class of antimycobacterials. Keri RS, Pandule SS, Budagumpi S, Nagaraja BM. Arch Pharm (Weinheim) 351 e1700325 (2018)

Articles citing this publication (18)

  1. Collateral sensitivity to novel thymidylate synthase inhibitors correlates with folate cycle enzymes impairment in cisplatin-resistant human ovarian cancer cells. Marverti G, Ligabue A, Paglietti G, Corona P, Piras S, Vitale G, Guerrieri D, Luciani R, Costi MP, Frassineti C, Moruzzi MS. Eur J Pharmacol 615 17-26 (2009)
  2. N-(4-(6,7-Disubstituted-quinolin-4-yloxy)-3-fluorophenyl)-2-oxo-3-phenylimidazolidine-1-carboxamides: a novel series of dual c-Met/VEGFR2 receptor tyrosine kinase inhibitors. Mannion M, Raeppel S, Claridge S, Zhou N, Saavedra O, Isakovic L, Zhan L, Gaudette F, Raeppel F, Déziel R, Beaulieu N, Nguyen H, Chute I, Beaulieu C, Dupont I, Robert MF, Lefebvre S, Dubay M, Rahil J, Wang J, Ste-Croix H, Robert Macleod A, Besterman JM, Vaisburg A. Bioorg Med Chem Lett 19 6552-6556 (2009)
  3. Discovery of 4-azaindoles as novel inhibitors of c-Met kinase. Porter J, Lumb S, Franklin RJ, Gascon-Simorte JM, Calmiano M, Riche KL, Lallemand B, Keyaerts J, Edwards H, Maloney A, Delgado J, King L, Foley A, Lecomte F, Reuberson J, Meier C, Batchelor M. Bioorg Med Chem Lett 19 2780-2784 (2009)
  4. Docking and quantitative structure-activity relationship studies for 3-fluoro-4-(pyrrolo[2,1-f][1,2,4]triazin-4-yloxy)aniline, 3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)aniline, and 4-(4-amino-2-fluorophenoxy)-2-pyridinylamine derivatives as c-Met kinase inhibitors. Caballero J, Quiliano M, Alzate-Morales JH, Zimic M, Deharo E. J Comput Aided Mol Des 25 349-369 (2011)
  5. Identification and synthesis of N'-(2-oxoindolin-3-ylidene)hydrazide derivatives against c-Met kinase. Liang Z, Zhang D, Ai J, Chen L, Wang H, Kong X, Zheng M, Liu H, Luo C, Geng M, Jiang H, Chen K. Bioorg Med Chem Lett 21 3749-3754 (2011)
  6. Synthesis and evaluation of quinoxaline derivatives as potential influenza NS1A protein inhibitors. You L, Cho EJ, Leavitt J, Ma LC, Montelione GT, Anslyn EV, Krug RM, Ellington A, Robertus JD. Bioorg Med Chem Lett 21 3007-3011 (2011)
  7. Pharmacophore modeling and virtual screening studies to identify new c-Met inhibitors. Tai W, Lu T, Yuan H, Wang F, Liu H, Lu S, Leng Y, Zhang W, Jiang Y, Chen Y. J Mol Model 18 3087-3100 (2012)
  8. Structural basis for selective small molecule kinase inhibition of activated c-Met. Rickert KW, Patel SB, Allison TJ, Byrne NJ, Darke PL, Ford RE, Guerin DJ, Hall DL, Kornienko M, Lu J, Munshi SK, Reid JC, Shipman JM, Stanton EF, Wilson KJ, Young JR, Soisson SM, Lumb KJ. J Biol Chem 286 11218-11225 (2011)
  9. Sulphonamido-quinoxalines: search for anticancer agent. Ingle R, Marathe R, Magar D, Patel HM, Surana SJ. Eur J Med Chem 65 168-186 (2013)
  10. Discovery of novel 6,7-disubstituted-4-phenoxyquinoline derivatives bearing 5-(aminomethylene)pyrimidine-2,4,6-trione moiety as c-Met kinase inhibitors. Tang Q, Zhang G, Du X, Zhu W, Li R, Lin H, Li P, Cheng M, Gong P, Zhao Y. Bioorg Med Chem 22 1236-1249 (2014)
  11. Molecular modeling studies and synthesis of novel quinoxaline derivatives with potential anticancer activity as inhibitors of c-Met kinase. Abbas HA, Al-Marhabi AR, Eissa SI, Ammar YA. Bioorg Med Chem 23 6560-6572 (2015)
  12. Synthesis and structure-activity relationship of aminopyridines with substituted benzoxazoles as c-Met kinase inhibitors. Lee J, Han SY, Jung H, Yang J, Choi JW, Chae CH, Park CH, Choi SU, Lee K, Ha JD, Lee CO, Ryu JW, Kim HR, Koh JS, Cho SY. Bioorg Med Chem Lett 22 4044-4048 (2012)
  13. Discovering potent inhibitors against c-Met kinase: molecular design, organic synthesis and bioassay. Liang Z, Ding X, Ai J, Kong X, Chen L, Chen L, Luo C, Geng M, Liu H, Chen K, Jiang H. Org Biomol Chem 10 421-430 (2012)
  14. Enhancing the cellular anti-proliferation activity of pyridazinones as c-met inhibitors using docking analysis. Xing W, Ai J, Jin S, Shi Z, Peng X, Wang L, Ji Y, Lu D, Liu Y, Geng M, Hu Y. Eur J Med Chem 95 302-312 (2015)
  15. Target identification, lead optimization and antitumor evaluation of some new 1,2,4-triazines as c-Met kinase inhibitors. El-Wakil MH, Ashour HM, Saudi MN, Hassan AM, Labouta IM. Bioorg Chem 73 154-169 (2017)
  16. Synthesis and biological evaluation of 2-amino-5-aryl-3-benzylthiopyridine scaffold based potent c-Met inhibitors. Zhang D, Zhang X, Ai J, Zhai Y, Liang Z, Wang Y, Chen Y, Li C, Zhao F, Jiang H, Geng M, Luo C, Liu H. Bioorg Med Chem 21 6804-6820 (2013)
  17. Apoptotic impact on Brugia malayi by sulphonamido-quinoxaline: search for a novel therapeutic rationale. Bhoj PS, Ingle RG, Goswami K, Jena L, Wadher S. Parasitol Res 117 1559-1572 (2018)
  18. The discovery of benzanilides as c-Met receptor tyrosine kinase inhibitors by a directed screening approach. Allen JV, Bardelle C, Blades K, Buttar D, Chapman L, Colclough N, Dossetter AG, Garner AP, Girdwood A, Lambert C, Leach AG, Law B, Major J, Plant H, Slater AM. Bioorg Med Chem Lett 21 5224-5229 (2011)


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