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Evaluation of a series of naphthamides as potent, orally active vascular endothelial growth factor receptor-2 tyrosine kinase inhibitors.

Weiss MM, Harmange JC, Polverino AJ, Bauer D, Berry L, Berry V, Borg G, Bready J, Chen D, Choquette D, Coxon A, DeMelfi T, Doerr N, Estrada J, Flynn J, Graceffa RF, Harriman SP, Kaufman S, La DS, Long A, Neervannan S, Patel VF, Potashman M, Regal K, Roveto PM, Schrag ML, Starnes C, Tasker A, Teffera Y, Whittington DA, Zanon R
J Med Chem 51 1668-80 (2008)
Cited: 16 times
EuropePMC logo PMID: 18324759

Abstract

We have previously shown N-arylnaphthamides can be potent inhibitors of vascular endothelial growth factor receptors (VEGFRs). N-Alkyl and N-unsubstituted naphthamides were prepared and found to yield nanomolar inhibitors of VEGFR-2 (KDR) with an improved selectivity profile against a panel of tyrosine and serine/threonine kinases. The inhibitory activity of this series was retained at the cellular level. Naphthamides 3, 20, and 22 exhibited good pharmacokinetics following oral dosing and showed potent inhibition of VEGF-induced angiogenesis in the rat corneal model. Once-daily oral administration of 22 for 14 days led to 85% inhibition of established HT29 colon cancer and Calu-6 lung cancer xenografts at doses of 10 and 20 mg/kg, respectively.

Reviews - 3b8r mentioned but not cited (1)

  1. Target-Based Small Molecule Drug Discovery for Colorectal Cancer: A Review of Molecular Pathways and In Silico Studies. Moshawih S, Lim AF, Ardianto C, Goh KW, Kifli N, Goh HP, Jarrar Q, Ming LC. Biomolecules 12 878 (2022)

Articles - 3b8r mentioned but not cited (6)

  1. Convolutional neural network scoring and minimization in the D3R 2017 community challenge. Sunseri J, King JE, Francoeur PG, Koes DR, Koes DR. J Comput Aided Mol Des 33 19-34 (2019)
  2. Novel VEGFR-2 kinase inhibitors identified by the back-to-front approach. Sanphanya K, Wattanapitayakul SK, Phowichit S, Fokin VV, Vajragupta O. Bioorg Med Chem Lett 23 2962-2967 (2013)
  3. Alchemical Grid Dock (AlGDock) calculations in the D3R Grand Challenge 3 : Binding free energies between flexible ligands and rigid receptors. Xie B, Minh DDL. J Comput Aided Mol Des 33 61-69 (2019)
  4. Resibufogenin Suppresses Triple-Negative Breast Cancer Angiogenesis by Blocking VEGFR2-Mediated Signaling Pathway. Yang T, Jiang YX, Wu Y, Lu D, Huang R, Wang LL, Wang SQ, Guan YY, Zhang H, Luan X. Front Pharmacol 12 682735 (2021)
  5. Understanding the polypharmacological anticancer effects of Xiao Chai Hu Tang via a computational pharmacological model. Zheng CS, Wu YS, Bao HJ, Xu XJ, Chen XQ, Ye HZ, Wu GW, Xu HF, Li XH, Chen JS, Liu XX. Exp Ther Med 7 1777-1783 (2014)
  6. Design, synthesis and biological evaluation of VEGFR-2/HDAC dual inhibitors as multitargeted antitumor agents based on fruquintinib and vorinostat. Gao Y, Li F, Ni X, Yang S, Liu H, Wu X, Liu J, Ma J. RSC Adv 13 28462-28480 (2023)


Reviews citing this publication (2)

  1. Structural biology contributions to tyrosine kinase drug discovery. Cowan-Jacob SW, Möbitz H, Fabbro D. Curr Opin Cell Biol 21 280-287 (2009)
  2. Update on lymphocyte specific kinase inhibitors: a patent survey. Martin MW, Machacek MR. Expert Opin Ther Pat 20 1573-1593 (2010)

Articles citing this publication (7)

  1. Selective flexibility of side-chain residues improves VEGFR-2 docking score using AutoDock Vina. Abreu RM, Froufe HJ, Queiroz MJ, Ferreira IC. Chem Biol Drug Des 79 530-534 (2012)
  2. Synthesis, Characterization and Anti-Cancer Activity of Hydrazide Derivatives Incorporating a Quinoline Moiety. Bingul M, Tan O, Gardner CR, Sutton SK, Arndt GM, Marshall GM, Cheung BB, Kumar N, Black DS. Molecules 21 E916 (2016)
  3. Molecular dynamics simulation and free energy calculation studies of kinase inhibitors binding to active and inactive conformations of VEGFR-2. Wu X, Wan S, Wang G, Jin H, Li Z, Tian Y, Zhu Z, Zhang J. J Mol Graph Model 56 103-112 (2015)
  4. Molecular modeling studies of vascular endothelial growth factor receptor tyrosine kinase inhibitors using QSAR and docking. Du J, Lei B, Qin J, Liu H, Yao X. J Mol Graph Model 27 642-654 (2009)
  5. Discovery of novel 1,2,3,4-tetrahydroisoquinolines and 3,4-dihydroisoquinoline-1(2H)-ones as potent and selective inhibitors of KDR: synthesis, SAR, and pharmacokinetic properties. Choquette D, Teffera Y, Polverino A, Harmange JC. Bioorg Med Chem Lett 18 4054-4058 (2008)
  6. Synthesis and biological evaluation of 3-substituted-indolin-2-one derivatives containing chloropyrrole moieties. Jin YZ, Fu DX, Ma N, Li ZC, Liu QH, Xiao L, Zhang RH. Molecules 16 9368-9385 (2011)
  7. Prevention of palatable diet-induced hyperphagia in rats by central injection of a VEGFR kinase inhibitor. Branch A, Bobilev A, Negrao NW, Cai H, Shen P. Behav Brain Res 278 506-513 (2015)


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