2,013
Views
8
CrossRef citations to date
0
Altmetric
Research Paper

Design, synthesis and biological evaluation of 4-bromo-N-(3,5-dimethoxyphenyl)benzamide derivatives as novel FGFR1 inhibitors for treatment of non-small cell lung cancer

, , , , , , , , , & show all
Pages 905-919 | Received 05 Feb 2018, Accepted 01 Apr 2018, Published online: 07 May 2018

References

  • Beenken A, Mohammadi M. The FGF family: biology, pathophysiology and therapy. Nat Rev Drug Discov 2009;8:235–53.
  • Knights V, Cook SJ. De-regulated FGF receptors as therapeutic targets in cancer. Pharmacol Ther 2010;125:105–17.
  • Turner N, Grose R. Fibroblast growth factor signalling: from development to cancer. Nat Rev Cancer 2010;10:116–29.
  • Brooks AN, Kilgour E, Smith PD. Molecular pathways: fibroblast growth factor signaling: a new therapeutic opportunity in cancer. Clin Cancer Res 2012;18:1855–62.
  • Belov AA, Mohammadi M. Molecular mechanisms of fibroblast growth factor signaling in physiology and pathology. Cold Spring Harb Perspect Biol 2013;5:a015958/1–/24.
  • Laestander C, Engstrom W. Role of fibroblast growth factors in elicitation of cell responses. Cell Prolif 2014;47:3–11.
  • Ronca R, Giacomini A, Rusnati M, et al. The potential of fibroblast growth factor/fibroblast growth factor receptor signaling as a therapeutic target in tumor angiogenesis. Expert Opin Ther Tar 2015;19:1361–77.
  • Touat M, Ileana E, Postel-Vinay S, et al. Targeting FGFR signaling in cancer. Clin Cancer Res 2015;21:2684–94.
  • Antoniu SA, Kolb MR. Intedanib, a triple kinase inhibitor of VEGFR, FGFR and PDGFR for the treatment of cancer and idiopathic pulmonary fibrosis. IDrugs 2010;13:332–45.
  • Helsten T, Schwaederle M, Kurzrock R. Fibroblast growth factor receptor signaling in hereditary and neoplastic disease: biologic and clinical implications. Cancer Metastasis Rev 2015;34:479–96.
  • Yamamoto Y, Matsui J, Matsushima T, et al. Lenvatinib, an angiogenesis inhibitor targeting VEGFR/FGFR, shows broad antitumor activity in human tumor xenograft models associated with microvessel density and pericyte coverage. Vascular Cell 2014;6:18.
  • Izzedine H, Ederhy S, Goldwasser F, et al. Management of hypertension in angiogenesis inhibitor-treated patients. Ann Oncol 2009;20:807–15.
  • Launay-Vacher V, Deray G. Hypertension and proteinuria: a class-effect of antiangiogenic therapies. Anti-Cancer Drugs 2009;20:81–2.
  • Ricciardi S, Tomao S, de Marinis F. Toxicity of targeted therapy in non-small-cell lung cancer management. Clin Lung Cancer 2009;10:28–35.
  • Gavine PR, Mooney L, Kilgour E, et al. AZD4547: an orally bioavailable, potent, and selective inhibitor of the fibroblast growth factor receptor tyrosine kinase family. Cancer Res 2012;72:2045–56.
  • Guagnano V, Furet P, Spanka C, et al. Discovery of 3-(2,6-dichloro-3,5-dimethoxy-phenyl)-1-{6-[4-(4-ethyl-piperazin-1-yl)-phenylamin o]-pyrimidin-4-yl}-1-methyl-urea (NVP-BGJ398), a potent and selective inhibitor of the fibroblast growth factor receptor family of receptor tyrosine kinase. J Med Chem 2011;54:7066–83.
  • Ebiike H, Taka N, Matsushita M, et al. Discovery of [5-amino-1-(2-methyl-3H-benzimidazol-5-yl)pyrazol-4-yl]-(1H-indol-2-yl)-methanone (CH5183284/Debio 1347), an orally available and selective fibroblast growth factor receptor (FGFR) inhibitor. J Med Chem 2016;59:10586–600.
  • Michael M, Bang YJ, Park YS, et al. A phase 1 study of LY2874455, an oral selective pan-FGFR inhibitor, in patients with advanced cancer. Targeted Oncol 2017;12:463–74.
  • Perera TPS, Jovcheva E, Mevellec L, et al. Discovery and pharmacological characterization of JNJ-42756493 (Erdafitinib), a functionally selective small-molecule FGFR family inhibitor. Mol Cancer Ther 2017;16:1010–20.
  • Mohammadi M, Froum S, Hamby JM, et al. Crystal structure of an angiogenesis inhibitor bound to the FGF receptor tyrosine kinase domain. EMBO J 1998;17:5896–904.
  • Norman RA, Schott AK, Andrews DM, et al. Protein-ligand crystal structures can guide the design of selective inhibitors of the FGFR tyrosine kinase. J Med Chem 2012;55:5003–12.
  • Villadolid J, Ersek JL, Fong MK, et al. Management of hyperglycemia from epidermal growth factor receptor (EGFR) tyrosine kinase inhibitors (TKIs) targeting T790M-mediated resistance. Transl Lung Cancer Res 2015;4:576–83.
  • Wang AL, Li XX, Wu H, et al. Discovery of (R)-1-(3-(4-Amino-3-(3-chloro-4-(pyridin-2-ylmethoxy)phenyl)-1H-pyrazolo[3,4-d]py-rimidin-1-yl)piperidin-1-yl)prop-2-en-1-one (CHMFL-EGFR-202) as a novel irreversible EGFR mutant kinase inhibitor with a distinct binding mode. J Med Chem 2017;60:2944–62.
  • Wang XB, Chen D, Yu SF, et al. Synthesis and evaluation of biological and antitumor activities of tetrahydrobenzothieno[2,3-d]pyrimidine derivatives as novel inhibitors of FGFR1. Chem BiolDrug Design 2016;87:499–507.
  • Ye FQ, Wang YW, Nian SY, et al. Synthesis and evaluation of biological and antitumor activities of 5,7-dimethyl-oxazolo[5,4-d]pyrimidine-4,6(5H,7H)-dione derivatives as novel inhibitors of FGFR1. J Enzyme Inhib Med Chem 2015;30:961–6.
  • Herbert C, Schieborr U, Saxena K, et al. Molecular mechanism of SSR128129E, an extracellularly acting, small-molecule, allosteric inhibitor of FGF receptor signaling. Cancer Cell 2013;23:489–501.
  • Zhang J, Yang PL, Gray NS. Targeting cancer with small molecule kinase inhibitors. Nat Rev Cancer 2009;9:28–39.
  • Chen CH, Liu YM, Pan SL, et al. Trichlorobenzene-substituted azaaryl compounds as novel FGFR inhibitors exhibiting potent antitumor activity in bladder cancer cells in vitro and in vivo. Oncotarget 2016;7:26374–87.
  • Jung SY, Yi JY, Kim MH, et al. IM-412 inhibits the invasion of human breast carcinoma cells by blocking FGFR-mediated signaling. Oncol Rep 2015;34:2731–7.
  • Xu W, Xie Y, Wang Q, et al. A novel fibroblast growth factor receptor 1 inhibitor protects against cartilage degradation in a murine model of osteoarthritis. Sci Rep 2016;6:24042.
  • Tucker JA, Klein T, Breed J, et al. Structural insights into FGFR kinase isoform selectivity: diverse binding modes of AZD4547 and ponatinib in complex with FGFR1 and FGFR4. Structure 2014;22:1764–74.
  • Chaudhari R, Li Z. PyMine: a PyMOL plugin to integrate and visualize data for drug discovery. BMC Res Note 2015;8:517