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SAR and evaluation of novel 5H-benzo[c][1,8]naphthyridin-6-one analogs as Aurora kinase inhibitors.

Karra S, Xiao Y, Chen X, Liu-Bujalski L, Huck B, Sutton A, Goutopoulos A, Askew B, Josephson K, Jiang X, Shutes A, Shankar V, Noonan T, Garcia-Berrios G, Dong R, Dhanabal M, Tian H, Wang Z, Clark A, Goodstal S
Bioorg Med Chem Lett 23 3081-7 (2013)
Cited: 8 times
EuropePMC logo PMID: 23570792

Abstract

Several potent Aurora kinase inhibitors derived from 5H-benzo[c][1,8]naphthyridin-6-one scaffold were identified. A crystal structure of Aurora kinase A in complex with an initial hit revealed a binding mode of the inhibitor within the ATP binding site and provided insight for structure-guided compound optimization. Subsequent SAR campaign provided a potent and selective pan Aurora inhibitor, which demonstrated potent target modulation and antiproliferative effects in the pancreatic cell line, MIAPaCa-2. Furthermore, this compound inhibited phosphorylation of histone H3 (pHH3) in mouse bone morrow upon oral administration, which is consistent with inhibition of Aurora kinase B activity.

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Reviews citing this publication (2)

  1. 1,8-Naphthyridine Derivatives: A Review of Multiple Biological Activities. Madaan A, Verma R, Kumar V, Singh AT, Jain SK, Jaggi M. Arch Pharm (Weinheim) 348 837-860 (2015)
  2. Synthetic Strategies in the Preparation of Phenanthridinones. Aleti RR, Festa AA, Voskressensky LG, Van der Eycken EV. Molecules 26 5560 (2021)

Articles citing this publication (4)

  1. Cheminformatics Analysis of Dynamic WNK-Inhibitor Interactions. Kuenemann MA, Fourches D. Mol Inform 37 e1700138 (2018)
  2. Discovery of 7-aryl-substituted (1,5-naphthyridin-4-yl)ureas as aurora kinase inhibitors. Defaux J, Antoine M, Le Borgne M, Schuster T, Seipelt I, Aicher B, Teifel M, Günther E, Gerlach M, Marchand P. ChemMedChem 9 217-232 (2014)
  3. Catalytic Enantioselective Birch-Heck Sequence for the Synthesis of Phenanthridinone Derivatives with an All-Carbon Quaternary Stereocenter. Sexton M, Malachowski WP, Yap GPA, Rachii D, Feldman G, Krasley AT, Chen Z, Tran MA, Wiley K, Matei A, Petersen S, Tien ST. J Org Chem 87 1154-1172 (2022)
  4. Nickel-Catalyzed Oxidative Decarboxylative Annulation for the Synthesis of Heterocycle-Containing Phenanthridinones. Honeycutt AP, Hoover JM. Org Lett 20 7216-7219 (2018)


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