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Inhibitors of the tyrosine kinase EphB4. Part 2: structure-based discovery and optimisation of 3,5-bis substituted anilinopyrimidines.

Bardelle C, Coleman T, Cross D, Davenport S, Kettle JG, Ko EJ, Leach AG, Mortlock A, Read J, Roberts NJ, Robins P, Williams EJ
Bioorg Med Chem Lett 18 5717-21 (2008)
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Cited: 27 times
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Abstract

Crystallographic studies of a range of 3-substituted anilinopyrimidine inhibitors of EphB4 have highlighted two alternative C-2 aniline conformations and this discovery has been exploited in the design of a highly potent series of 3,5-disubstituted anilinopyrimidines. The observed range of cellular activities has been rationalised on the basis of physicochemical and structural characteristics.

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  1. Eph receptors and ephrins in cancer: bidirectional signalling and beyond. Pasquale EB. Nat Rev Cancer 10 165-180 (2010)
  2. Eph receptors and ephrins as targets for cancer therapy. Xi HQ, Wu XS, Wei B, Chen L. J Cell Mol Med 16 2894-2909 (2012)
  3. EphB4: A promising target for upper aerodigestive malignancies. Salgia R, Kulkarni P, Gill PS. Biochim Biophys Acta Rev Cancer 1869 128-137 (2018)
  4. The critical role of the interplays of EphrinB2/EphB4 and VEGF in the induction of angiogenesis. Du E, Li X, He S, Li X, He S. Mol Biol Rep 47 4681-4690 (2020)
  5. New strategies in achieving antiangiogenic effect: Multiplex inhibitors suppressing compensatory activations of RTKs. Shan Y, Wang B, Zhang J. Med Res Rev 38 1674-1705 (2018)

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  1. The small molecule specific EphB4 kinase inhibitor NVP-BHG712 inhibits VEGF driven angiogenesis. Martiny-Baron G, Holzer P, Billy E, Schnell C, Brueggen J, Ferretti M, Schmiedeberg N, Wood JM, Furet P, Imbach P. Angiogenesis 13 259-267 (2010)
  2. Eph receptors and ephrin ligands: important players in angiogenesis and tumor angiogenesis. Mosch B, Reissenweber B, Neuber C, Pietzsch J. J Oncol 2010 135285 (2010)
  3. The EphB4 receptor tyrosine kinase promotes lung cancer growth: a potential novel therapeutic target. Ferguson BD, Liu R, Rolle CE, Tan YH, Krasnoperov V, Kanteti R, Tretiakova MS, Cervantes GM, Hasina R, Hseu RD, Iafrate AJ, Karrison T, Ferguson MK, Husain AN, Faoro L, Vokes EE, Gill PS, Salgia R. PLoS One 8 e67668 (2013)
  4. Development of o-chlorophenyl substituted pyrimidines as exceptionally potent aurora kinase inhibitors. Lawrence HR, Martin MP, Luo Y, Pireddu R, Yang H, Gevariya H, Ozcan S, Zhu JY, Kendig R, Rodriguez M, Elias R, Cheng JQ, Sebti SM, Schonbrunn E, Lawrence NJ. J Med Chem 55 7392-7416 (2012)
  5. Dispensing processes impact apparent biological activity as determined by computational and statistical analyses. Ekins S, Olechno J, Williams AJ. PLoS One 8 e62325 (2013)
  6. qFit-ligand Reveals Widespread Conformational Heterogeneity of Drug-Like Molecules in X-Ray Electron Density Maps. van Zundert GCP, Hudson BM, de Oliveira SHP, Keedy DA, Fonseca R, Heliou A, Suresh P, Borrelli K, Day T, Fraser JS, van den Bedem H. J Med Chem 61 11183-11198 (2018)
  7. Inhibitors of the tyrosine kinase EphB4. Part 4: Discovery and optimization of a benzylic alcohol series. Barlaam B, Ducray R, Lambert-van der Brempt C, Plé P, Bardelle C, Brooks N, Coleman T, Cross D, Kettle JG, Read J. Bioorg Med Chem Lett 21 2207-2211 (2011)
  8. Fluorine-18 radiolabeling and radiopharmacological characterization of a benzodioxolylpyrimidine-based radiotracer targeting the receptor tyrosine kinase EphB4. Mamat C, Mosch B, Neuber C, Köckerling M, Bergmann R, Pietzsch J. ChemMedChem 7 1991-2003 (2012)
  9. An efficient bioorthogonal strategy using CuAAC click chemistry for radiofluorinations of SNEW peptides and the role of copper depletion. Pretze M, Kuchar M, Bergmann R, Steinbach J, Pietzsch J, Mamat C. ChemMedChem 8 935-945 (2013)
  10. A novel benzodioxole-containing inhibitor of Toxoplasma gondii growth alters the parasite cell cycle. Kamau E, Meehan T, Lavine MD, Arrizabalaga G, Mustata Wilson G, Boyle J. Antimicrob Agents Chemother 55 5438-5451 (2011)
  11. Completing the structural family portrait of the human EphB tyrosine kinase domains. Overman RC, Debreczeni JE, Truman CM, McAlister MS, Attwood TK. Protein Sci 23 627-638 (2014)
  12. Novel EPHB4 Receptor Tyrosine Kinase Mutations and Kinomic Pathway Analysis in Lung Cancer. Ferguson BD, Carol Tan YH, Kanteti RS, Liu R, Gayed MJ, Vokes EE, Ferguson MK, John Iafrate A, Gill PS, Salgia R. Sci Rep 5 10641 (2015)
  13. Sampling Conformational Changes of Bound Ligands Using Nonequilibrium Candidate Monte Carlo and Molecular Dynamics. Sasmal S, Gill SC, Lim NM, Mobley DL. J Chem Theory Comput 16 1854-1865 (2020)
  14. Biochemical and biophysical characterization of four EphB kinase domains reveals contrasting thermodynamic, kinetic and inhibition profiles. Overman RC, Debreczeni JE, Truman CM, McAlister MS, Attwood TK. Biosci Rep 33 e00040 (2013)
  15. Elucidating the multiple roles of hydration for accurate protein-ligand binding prediction via deep learning. Mahmoud AH, Masters MR, Yang Y, Lill MA. Commun Chem 3 19 (2020)
  16. Preparation of a novel radiotracer targeting the EphB4 receptor via radiofluorination using spiro azetidinium salts as precursor. Wiemer J, Steinbach J, Pietzsch J, Mamat C. J Labelled Comp Radiopharm 60 489-498 (2017)
  17. Biomimetic Aerobic C-H Olefination of Cyclic Enaminones at Room Temperature: Development toward the Synthesis of 1,3,5-Trisubstituted Benzenes. Yu YY, Georg GI. Adv Synth Catal 356 1359-1369 (2014)
  18. EphB4 cellular kinase activity assayed using an enzymatic protein interaction system. Wehrman T, Nguyen M, Feng W, Bader B. Assay Drug Dev Technol 11 237-243 (2013)
  19. Identifying potential selective fluorescent probes for cancer-associated protein carbonic anhydrase IX using a computational approach. Kamstra RL, Floriano WB. J Mol Graph Model 54 184-193 (2014)
  20. N-(2,4)-dinitrophenyl-L-arginine Interacts with EphB4 and Functions as an EphB4 Kinase Modulator. Kamstra RL, Freywald A, Floriano WB. Chem Biol Drug Des 86 476-486 (2015)
  21. Pneumatic conveying printing technique for bioprinting applications. Brand I, Groß I, Li D, Zhang Y, Bräuer AU. RSC Adv 9 40910-40916 (2019)


Related citations provided by authors (1)

  1. Inhibitors of the tyrosine kinase EphB4. Part 1: Structure-based design and optimization of a series of 2,4-bis-anilinopyrimidines.. Bardelle C, Cross D, Davenport S, Kettle JG, Ko EJ, Leach AG, Mortlock A, Read J, Roberts NJ, Robins P, Williams EJ Bioorg Med Chem Lett 18 2776-80 (2008)

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