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Structure-based design of imidazo[1,2-a]pyrazine derivatives as selective inhibitors of Aurora-A kinase in cells.

Bouloc N, Large JM, Kosmopoulou M, Sun C, Faisal A, Matteucci M, Reynisson J, Brown N, Atrash B, Blagg J, McDonald E, Linardopoulos S, Bayliss R, Bavetsias V
Bioorg Med Chem Lett 20 5988-93 (2010)
Cited: 13 times
EuropePMC logo PMID: 20833547

Abstract

Co-crystallisation of the imidazo[1,2-a]pyrazine derivative 15 (3-chloro-N-(4-morpholinophenyl)-6-(pyridin-3-yl)imidazo[1,2-a]pyrazin-8-amine) with Aurora-A provided an insight into the interactions of this class of compound with Aurora kinases. This led to the design and synthesis of potent Aurora-A inhibitors demonstrating up to 70-fold selectivity in cell-based Aurora kinase pharmacodynamic biomarker assays.

Reviews citing this publication (5)

  1. On the molecular mechanisms of mitotic kinase activation. Bayliss R, Fry A, Haq T, Yeoh S. Open Biol 2 120136 (2012)
  2. The azaindole framework in the design of kinase inhibitors. Mérour JY, Buron F, Plé K, Bonnet P, Routier S. Molecules 19 19935-19979 (2014)
  3. Synthetic approaches and pharmaceutical applications of chloro-containing molecules for drug discovery: A critical review. Fang WY, Ravindar L, Rakesh KP, Manukumar HM, Shantharam CS, Alharbi NS, Qin HL. Eur J Med Chem 173 117-153 (2019)
  4. Recent advances in development of imidazo[1,2-a]pyrazines: synthesis, reactivity and their biological applications. Goel R, Luxami V, Paul K. Org Biomol Chem 13 3525-3555 (2015)
  5. The hunt for antimitotic agents: an overview of structure-based design strategies. Dube D, Tiwari P, Kaur P. Expert Opin Drug Discov 11 579-597 (2016)

Articles citing this publication (8)

  1. A Cell Biologist's Field Guide to Aurora Kinase Inhibitors. de Groot CO, Hsia JE, Anzola JV, Motamedi A, Yoon M, Wong YL, Jenkins D, Lee HJ, Martinez MB, Davis RL, Gahman TC, Desai A, Shiau AK. Front Oncol 5 285 (2015)
  2. Optimization of imidazo[4,5-b]pyridine-based kinase inhibitors: identification of a dual FLT3/Aurora kinase inhibitor as an orally bioavailable preclinical development candidate for the treatment of acute myeloid leukemia. Bavetsias V, Crumpler S, Sun C, Avery S, Atrash B, Faisal A, Moore AS, Kosmopoulou M, Brown N, Sheldrake PW, Bush K, Henley A, Box G, Valenti M, de Haven Brandon A, Raynaud FI, Workman P, Eccles SA, Bayliss R, Linardopoulos S, Blagg J. J Med Chem 55 8721-8734 (2012)
  3. Aurora isoform selectivity: design and synthesis of imidazo[4,5-b]pyridine derivatives as highly selective inhibitors of Aurora-A kinase in cells. Bavetsias V, Faisal A, Crumpler S, Brown N, Kosmopoulou M, Joshi A, Atrash B, Pérez-Fuertes Y, Schmitt JA, Boxall KJ, Burke R, Sun C, Avery S, Bush K, Henley A, Raynaud FI, Workman P, Bayliss R, Linardopoulos S, Blagg J. J Med Chem 56 9122-9135 (2013)
  4. 2- and 3-substituted imidazo[1,2-a]pyrazines as inhibitors of bacterial type IV secretion. Sayer JR, Walldén K, Pesnot T, Campbell F, Gane PJ, Simone M, Koss H, Buelens F, Boyle TP, Selwood DL, Waksman G, Tabor AB. Bioorg Med Chem 22 6459-6470 (2014)
  5. Purine-benzimidazole hybrids: synthesis, single crystal determination and in vitro evaluation of antitumor activities. Sharma A, Luxami V, Paul K. Eur J Med Chem 93 414-422 (2015)
  6. 7-(Pyrazol-4-yl)-3H-imidazo[4,5-b]pyridine-based derivatives for kinase inhibition: Co-crystallisation studies with Aurora-A reveal distinct differences in the orientation of the pyrazole N1-substituent. Bavetsias V, Pérez-Fuertes Y, McIntyre PJ, Atrash B, Kosmopoulou M, O'Fee L, Burke R, Sun C, Faisal A, Bush K, Avery S, Henley A, Raynaud FI, Linardopoulos S, Bayliss R, Blagg J. Bioorg Med Chem Lett 25 4203-4209 (2015)
  7. Detection of Ligand-induced Conformational Changes in the Activation Loop of Aurora-A Kinase by PELDOR Spectroscopy. Burgess SG, Grazia Concilio M, Bayliss R, Fielding AJ. ChemistryOpen 5 531-534 (2016)
  8. A highly efficient precatalytic system (XPhos-PdG2) for the Suzuki-Miyaura cross-coupling of 7-chloro-1H-pyrrolo[2,3-c]pyridine employing low catalyst loading. Savitha B, Reddy EK, Parthasarathi D, Pakkath R, Karuvalam RP, Ananda Kumar CS, Haridas KR, Syed Ali Padusha M, Sajith AM. Mol Divers 23 697-707 (2019)


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