1,071
Views
2
CrossRef citations to date
0
Altmetric
Research Papers

Synthesis and biological activity evaluation of 3-(hetero) arylideneindolin-2-ones as potential c-Src inhibitors

, , , , , , , , & ORCID Icon show all
Pages 2382-2394 | Received 15 Jun 2022, Accepted 21 Aug 2022, Published online: 01 Sep 2022

References

  • Simatou A, Simatos G, Goulielmaki M, et al. Historical retrospective of the SRC oncogene and new perspectives. Mol Clin Oncol 2020;13:1–10.
  • Parsons SJ, Parsons JT. Src family kinases, key regulators of signal transduction. Oncogene 2004;23:7906–9.
  • Brown MT, Cooper JA. Regulation, substrates and functions of src. Biochimica et Biophysica Acta (BBA) – Reviews on Cancer 1996;1287:121–49.
  • Playford MP, Schaller MD. The interplay between Src and integrins in normal and tumor biology. Oncogene 2004;23:7928–46.
  • Sigal CT, Zhou W, Buser CA, et al. Amino-terminal basic residues of Src mediate membrane binding through electrostatic interaction with acidic phospholipids. Proc Natl Acad Sci USA 1994;91:12253–7.
  • Boggon TJ, Eck MJ. Structure and regulation of Src family kinases. Oncogene 2004;23:7918–27.
  • Amata I, Maffei M, Pons M. Phosphorylation of unique domains of Src family kinases. Front Genet 2014;5:181.
  • Roskoski R. Src kinase regulation by phosphorylation and dephosphorylation. Biochem Biophys Res Commun 2005;331:1–14.
  • McLachlan RW, Kraemer A, Helwani FM, et al. E-cadherin adhesion activates c-Src signaling at cell–cell contacts. Mol Biol Cell 2007;18:3214–23.
  • Patel A, Sabbineni H, Clarke A, Somanath PR. Novel roles of Src in cancer cell epithelial-to-mesenchymal transition, vascular permeability, microinvasion and metastasis. Life Sci 2016;157:52–61.
  • Maa MC, Leu TH, McCarley DJ, et al. Potentiation of epidermal growth factor receptor-mediated oncogenesis by c-Src: implications for the etiology of multiple human cancers. Proc Natl Acad Sci 1995;92:6981–5.
  • Shah K, Vincent F. Divergent roles of c-src in controlling platelet-derived growth factor-dependent signaling in fibroblasts. Mol Biol Cell 2005;16:5418–32.
  • Ishizawar RC, Miyake T, Parsons SJ. c-Src modulates ErbB2 and ErbB3 heterocomplex formation and function. Oncogene 2007;26:3503–10.
  • Rahimi N, Hung W, Tremblay E, et al. c-Src kinase activity is required for hepatocyte growth factor-induced motility and anchorage-independent growth of mammary carcinoma cells*. J Biol Chem 1998;273:33714–21.
  • Calgani A, Vignaroli G, Zamperini C, et al. Suppression of SRC signaling is effective in reducing synergy between glioblastoma and stromal cells. Mol Cancer Ther 2016;15:1535–44.
  • González L, Agulló-Ortuño MT, García-Martínez JM, et al. Role of c-Src in human MCF7 breast cancer cell tumorigenesis*. J Biol Chem 2006;281:20851–64.
  • Zhang J, Kalyankrishna S, Wislez M, et al. Src-family kinases are activated in non-small cell lung cancer and promote the survival of epidermal growth factor receptor-dependent cell lines. Am J Pathol 2007;170:366–76.
  • Schweppe RE, Kerege AA, French JD, et al. Inhibition of Src with AZD0530 reveals the Src-focal adhesion kinase complex as a novel therapeutic target in papillary and anaplastic thyroid cancer. J Clin Endocrinol Metabolism 2009;94:2199–203.
  • Lowe C, Yoneda T, Boyce BF, et al. Osteopetrosis in Src-deficient mice is due to an autonomous defect of osteoclasts. Proc Natl Acad Sci 1993;90:4485–9.
  • Rucci N, Susa M, Teti A. Inhibition of protein kinase c-Src as a therapeutic approach for cancer and bone metastases. Anti-Cancer Agents Med Chem 2008;8:342–9.
  • Jin W. Regulation of Src family kinases during colorectal cancer development and its clinical implications. Cancers 2020;12:1339.
  • Lutz MP, Eßer IBS, Flossmann-Kast BBM, et al. Overexpression and activation of the tyrosine kinase Src in human pancreatic carcinoma. Biochem Biophys Res Commun 1998;243:503–8.
  • Varkaris A, Katsiampoura AD, Araujo JC, et al. Src signaling pathways in prostate cancer. Cancer Metastasis Rev 2014;33:595–606.
  • Belli S, Esposito D, Servetto A, et al. c-Src and EGFR inhibition in molecular cancer therapy: what else can we improve? Cancers. 2020;12:1489.
  • Rivera-Torres J, San José E. Src tyrosine kinase inhibitors: new perspectives on their immune, antiviral, and senotherapeutic potential. Front Pharmacol 2019;10:1011.
  • Musumeci F, Brullo C, Grossi G, et al. Identification of new pyrrolo[2,3-d]pyrimidines as Src tyrosine kinase inhibitors in vitro active against Glioblastoma. Eur J Med Chem 2017;127:369–78.
  • Ceccherini E, Indovina P, Zamperini C, et al. SRC family kinase inhibition through a new pyrazolo[3,4- d] pyrimidine derivative as a feasible approach for glioblastoma treatment. J Cell Biochem 2015;116:856–63.
  • Gnoni A, Marech I, Silvestris N, et al. Dasatinib: an anti-tumour agent via Src inhibition. Current Drug Targets 2011;12:563–78.
  • Steinbach A, Clark SM, Clemmons AB. Bosutinib: a novel src/abl kinase inhibitor for chronic myelogenous leukemia. J Adv Pract Oncol 2013;4:451–5.
  • Hennequin LF, Allen J, Breed J, et al. N-(5-Chloro-1,3-benzodioxol-4-yl)-7-[2-(4-methylpiperazin-1-yl)ethoxy]-5- (tetrahydro-2H-pyran-4-yloxy)quinazolin-4-amine, a novel, highly selective, orally available, dual-specific c-Src/Abl kinase inhibitor. J Med Chem 2006;49:6465–88.
  • Cooper MR, Yi SY, Alghamdi W, et al. Vandetanib for the treatment of medullary thyroid carcinoma. Ann Pharmacother 2014;48:387–94.
  • Tanimura K, Yamasaki K, Okuhiro Y, et al. Monitoring ponatinib in a child with philadelphia chromosome-positive acute lymphoblastic leukemia. Case Rep Oncol 2021;14:24–8.
  • Gurbani D, Du G, Henning NJ, et al. Structure and characterization of a covalent inhibitor of Src kinase. Front Mol Biosci 2020;7:81–9.
  • Temps C, Lietha D, Webb ER, et al. A conformation selective mode of inhibiting SRC improves drug efficacy and tolerability. Cancer Res 2021;81:5438–50.
  • Hong DS, Sen S, Park H, et al. A phase I, open-label, multicenter, first-in-human study of the safety, tolerability, pharmacokinetics, and antitumor activity of TPX-0022, a novel MET/CSF1R/SRC inhibitor, in patients with advanced solid tumors harboring genetic alterations in MET. J Clin Oncol 2020;38:TPS3663–TPS3663.
  • Wang X, Ren R, Xu Z, et al. Tirbanibulin attenuates pulmonary fibrosis by modulating Src/STAT3 signaling. Front Pharmacol 2021;12:693906.
  • Markham A, Duggan S. Tirbanibulin: first approval. Drugs 2021;81:509–13.
  • Cincinelli R, Musso L, Merlini L, et al. 7-Azaindole-1-carboxamides as a new class of PARP-1 inhibitors. Bioorg Med Chem 2014;22:1089–103.
  • Aiwale TS, Dallavalle S. Efficient synthesis of 3,7-Diaryl-1,4-dihydro[1,2,4]triazolo[5,1-c][1,2,4]triazines. Synthesis 2012;44:3055–8.
  • Cincinelli R, Cassinelli G, Dallavalle S, et al. Synthesis, modeling, and RET protein kinase inhibitory activity of 3- and 4-Substituted β-Carbolin-1-ones. J Med Chem 2008;51:7777–87.
  • Musso L, Cincinelli R, Zuco V, et al. 3-Arylidene-N-hydroxyoxindoles: a new class of compounds endowed with antitumor activity. ChemMedChem 2016;11:1700–4.
  • Rizzi E, Cassinelli G, Dallavalle S, et al. Synthesis and RET protein kinase inhibitory activity of 3-arylureidobenzylidene-indolin-2-ones. Bioorg Med Chem Lett 2007;17:3962–8.
  • Cautain B, Castillo F, Musso L, et al. Discovery of a novel, isothiazolonaphthoquinone-based small molecule activator of FOXO nuclear-cytoplasmic shuttling. PLOS One 2016;11:e0167491.
  • Cincinelli R, Musso L, Beretta G, Dallavalle S. 4-Quinolone fused heterocyclic ring systems by intramolecular reactions of 4-quinolone-2-carboxamides. Tetrahedron 2014;70:9797–804.
  • Musso L, Cincinelli R, Giannini G, et al. Synthesis of 5,6-dihydro-4H-benzo[d]isoxazol-7-one and 5,6-dihydro-4H-isoxazolo[5,4-c]pyridin-7-one Derivatives as Potential Hsp90 Inhibitors. Chemical Biology & Drug Design 2015;86:1030–5.
  • Höttecke N, Liebeck M, Baumann K, et al. Inhibition of γ-secretase by the CK1 inhibitor IC261 does not depend on CK1δ. Bioorg Med Chem Lett 2010;20:2958–63.
  • la Pietra V, Sartini S, Botta L, et al. Challenging clinically unresponsive medullary thyroid cancer: discovery and pharmacological activity of novel RET inhibitors. Eur J Med Chem 2018;150:491–505.
  • Chu W, Zhou D, Gaba V, et al. Design, synthesis, and characterization of 3-(Benzylidene)indolin-2-one derivatives as ligands for α-synuclein fibrils. J Med Chem 2015;58:6002–17.
  • Ngai MH, So CL, Sullivan MB, et al. Photoinduced isomerization and hepatoxicities of semaxanib, sunitinib and related 3-substituted indolin-2-ones. ChemMedChem 2016;11:72–80.
  • Chen X, Yang T, Deivasigamani A, et al. N′-Alkylaminosulfonyl analogues of 6-fluorobenzylideneindolinones with desirable physicochemical profiles and potent growth inhibitory activities on hepatocellular carcinoma. ChemMedChem 2015;10:1548–58.