Design, synthesis and biological evaluation of novel 1H-1,2,4-triazole, benzothiazole and indazole-based derivatives as potent FGFR1 inhibitors viafragment-based virtual screening

References

• Anand P, Kunnumakara A, Sundaram C, et al. Cancer is a preventable disease that requires major lifestyle changes. Pharm Res 2008;25:2097–116.
   PubMed Web of Science ®Google Scholar
• Siemann DW, Chaplin DJ, Horsman MR. Vascular-targeting therapies for treatment of malignant disease. Cancer 2004;100:2491–9.
   PubMed Web of Science ®Google Scholar
• Traxler P, Furet P. Strategies toward the design of novel and selective protein tyrosine kinase inhibitors. Pharmacol Ther 1999;82:195–206.
   PubMed Web of Science ®Google Scholar
• Sharma PS, Sharma R, Tyagi T. Receptor tyrosine kinase inhibitors as potent weapons in war against cancers. Curr Pharm Des 2009;15:758–76.
   PubMed Web of Science ®Google Scholar
• Ocana A, Serrano R, Calero R, Pandiella A. Novel tyrosine kinase inhibitors in the treatment of cancer. Curr Drug Targets 2009;10:575–6.
   PubMed Web of Science ®Google Scholar
• Huang M, Shen A, Ding J, Geng M. Molecularly targeted cancer therapy: some lessons from the past decade. Trends Pharmacol Sci 2014;35:41–50.
   PubMed Web of Science ®Google Scholar
• Clark JD, Flanagan ME, Telliez JB. Discovery and development of Janus Kinase (JAK) inhibitors for inflammatory diseases: miniperspective. J Med Chem 2014;57:5023–38.
   PubMed Web of Science ®Google Scholar
• Touat M, Ileana E, Postel-Vinay S, et al. Targeting FGFR signaling in cancer. Clin Cancer Res 2015;21:2684–94.
   PubMed Web of Science ®Google Scholar
• Carter EP, Fearon AE, Grose RP. Careless talk costs lives: fibroblast growth factor receptor signalling and the consequences of pathway malfunction. Trends Cell Biol 2015;25:221–33.
   PubMed Web of Science ®Google Scholar
• Dieci MV, Arnedos M, Andre F, Soria JC. Fibroblast growth factor receptor inhibitors as a cancer treatment: from a biologic rationale to medical perspectives. Cancer Discovery 2013;3:264–79.
   PubMed Web of Science ®Google Scholar
• Singh D, Chan JM, Zoppoli P, et al. Transforming fusions of FGFR and TACC genes in human glioblastoma. Science 2012;337:1231–5.
   PubMed Web of Science ®Google Scholar
• Wu YM, Su F, Kalyana-Sundaram S, et al. Identification of targetable FGFR gene fusions in diverse cancers. Cancer Discovery 2013;3:636–47.
   PubMed Web of Science ®Google Scholar
• Helsten T, Elkin S, Arthur E, et al. The FGFR landscape in cancer: analysis of 4,853 tumors by next-generation sequencing. Clin Cancer Res 2016;22:259–67.
   PubMed Web of Science ®Google Scholar
• Hilberg F, Roth GJ, Krssak M, et al. BIBF 1120: triple angiokinase inhibitor with sustained receptor blockade and good antitumor efficacy. Cancer Res 2008;68:4774–82.
   PubMed Web of Science ®Google Scholar
• Roth GJ, Heckel A, Colbatzky F, et al. Design, synthesis, and evaluation of indolinones as triple angiokinase inhibitors and the discovery of a highly specific 6-methoxycarbonyl-substituted indolinone (BIBF 1120). J Med Chem 2009;52:4466–80.
   PubMed Web of Science ®Google Scholar
• Gozgit JM, Wong MJ, Moran L, et al. Ponatinib (AP24534), a multitargeted pan-FGFR inhibitor with activity in multiple FGFR-amplified or mutated cancer models. Mol Cancer Ther 2012;11:690–9.
   PubMed Web of Science ®Google Scholar
• 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-ylphenylamino] -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.
   PubMed Web of Science ®Google Scholar
• Zhao GS, Li WY, Chen DH, et al. A novel, selective inhibitor of fibroblast growth factor receptors that shows a potent broad spectrum of antitumor activity in several tumor xenograft models. Mol Cancer Ther 2011;10:2200–10.
   PubMed Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• Perera TPS, Jovcheva E, Mevellec L, et al. Discovery and pharmacological characterization of JNJ-42756493 (erdafitinib), a functionally selective smallmolecule FGFR family inhibitor. Mol Cancer Ther 2017;16:1010–20.
   PubMed Web of Science ®Google Scholar
• Nakanishi Y, Akiyama N, Tsukaguchi T, et al. The fibroblast growth factor receptor genetic status as a potential predictor of the sensitivity to CH5183284/Debio 1347, a novel selective FGFR inhibitor. Mol Cancer Ther 2014;13:2547–58.
   PubMed Web of Science ®Google Scholar
• Liu J, Peng X, Dai Y, et al. Design, synthesis and biological evaluation of novel FGFR inhibitors bearing indazole scaffold. Org Biomol Chem 2015;13:7643–54.
   PubMed Web of Science ®Google Scholar
• Yosaatmadja Y, Patterson AV, Smaill JB, Squire CJ. The 1.65 Å resolution structure of the complex of AZD4547 with the kinase domain of FGFR1 displays exquisite molecular recognition. Acta Crystallogr 2015;71:525–33.
   Google Scholar
• Zhang J, Yang PL, Gray NS. Targeting cancer with small molecule kinase inhibitors. Nat Rev Cancer 2009;9:28–39.
   PubMed Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• Miyaura N, Suzuki A. Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem Rev 1995;95:2457–85.
   Web of Science ®Google Scholar
• Ken AB, Timothy DO, Erik V, et al. Discovery of the irreversible covalent FGFR inhibitor 8-(3-(4-acryloylpiperazin-1-yl)propyl)-6-(2,6-dichloro-3,5-dimethoxyphenyl)-2-(methylamino)pyrido[2,3-d]pyrimidin-7(8H)‑one (PRN1371) for the treatment of solid tumors. J Med Chem 2017;60:6516–27.
   PubMed Web of Science ®Google Scholar
• Li X, Guise CP, Taghipouran R, et al. 2-Oxo-3, 4-dihydropyrimido[4, 5-d]pyrimidinyl derivatives as new irreversible pan fibroblast growth factor receptor (FGFR) inhibitors. Eur J Med Chem 2017;135:531–43.
   PubMed Web of Science ®Google Scholar
• Lu X, Chen H, Patterson AV, et al. Fibroblast growth factor receptor 4 (FGFR4) selective inhibitors as hepatocellular carcinoma therapy: advances and prospects. J Med Chem 2019;62:2905–15.
   PubMedGoogle Scholar