Benzofuran–appended 4-aminoquinazoline hybrids as epidermal growth factor receptor tyrosine kinase inhibitors: synthesis, biological evaluation and molecular docking studies

References

• Woodburn JR. The epidermal growth factor receptor and its inhibition in cancer therapy. Pharmacol Ther 1999;82:241–50.
   PubMed Web of Science ®Google Scholar
• Dobrusin EM, Fry DW. Chapter 18. Protein tyrosine kinases and cancer. Annu Rep Med Chem 1992;27:169–78.
   Google Scholar
• Zwick E, Bange J, Ullrich A. Receptor tyrosine kinase signalling as a target for cancer intervention strategies. Endocr Relat Cancer 2001;8:161–73.
   PubMed Web of Science ®Google Scholar
• Fry DW, Kraker AJ, McMichael A, et al. A specific inhibitor of the epidermal growth factor receptor tyrosine kinase. Science 1994;265:1093–5.
   PubMed Web of Science ®Google Scholar
• Bridges AJ. Chemical inhibitors of protein kinases. Chem Rev 2001;101:2541–71.
   PubMed Web of Science ®Google Scholar
• Zhao Z-Q, Yu Z-Y, Li J, Ouyang X-N. Gefitinib induces lung cancer cell autophagy and apoptosis via blockade of the PI3K/AKT/mTOR pathway. Oncol Lett 2016;12:63–8.
   PubMed Web of Science ®Google Scholar
• Ismail RSM, Ismail NSM, Abuserii A, El Ella DAA. Recent advances in 4-aminoquinazoline based scaffold derivatives targeting EGFR kinases as anticancer agents. Future J Pharm Sci 2016;2:9–19.
   Web of Science ®Google Scholar
• Medinger M, Esser N, Zirrgiebel U, et al. Antitumor and antiangiogenic activity of cediranib in a preclinical model of renal cell carcinoma. Anticancer Res 2009;29:5065–76.
   PubMed Web of Science ®Google Scholar
• Wedge SR, Kendrew J, Hennequin LF, et al. AZD2171: A highly potent, orally bioavailable, vascular endothelial growth factor receptor-2 tyrosine kinase inhibitor for the treatment of cancer. Cancer Res 2005;65:4389–400.
   PubMed Web of Science ®Google Scholar
• Paumo HK, Makhafola JT, Mphahlele MJ. Synthesis and in vitro cytotoxic properties of polycarbo-substituted 4-(arylamino)quinazolines. Molecules 2016;21:1366–83.
   Web of Science ®Google Scholar
• Garofalo A, Goossens L, Baldeyrou B, et al. Design, synthesis, and DNA-binding of N-alkyl(anilino)quinazoline derivatives. J Med Chem 2010;53:8089–103.
   PubMed Web of Science ®Google Scholar
• Nevagi RJ, Dighe SN, Dighe SN. Biological and medicinal significance of benzofuran. Eur J Med Chem 2015;97:561–81.
   PubMed Web of Science ®Google Scholar
• Cooper LC, Chicchi GG, Dinnell K, et al. 2-Aryl indole NK1 receptor antagonists: Optimisation of indole substitution. Bioorg Med Chem Lett 2001;11:1233–6.
   PubMed Web of Science ®Google Scholar
• Ando K, Kawamura Y, Akai Y, et al. Preparation of 2-, 3-, 4- and 7-(2-alkylcarbamoyl-1-alkylvinyl)benzo[b]furans and their BLT1 and/or BLT2 inhibitory activities. Org Biomol Chem 2008;6:296–307.
   PubMed Web of Science ®Google Scholar
• Galal SA, Abd El-All AS, Abdallah MM, El-Diwani HI. Synthesis of potent antitumor and antiviral benzofuran derivatives. Bioorg Med Chem Lett 2009;19:2420–8.
   PubMed Web of Science ®Google Scholar
• Hwang JW, Choi DH, Jeon J-H, et al. Facile preparation of 2-arylbenzo[b]furan molecules and their anti-inflammatory effects. Bull Korean Chem Soc 2010;31:965–70.
   Web of Science ®Google Scholar
• Eiblmaier M, Meyer LA, Watson MA, et al. Correlating EGFR expression with receptor-binding properties and internalization of 64Cu-DOTA-cetuximab in 5 cervical cancer cell lines. J Nucl Med 2008;49:1472–9.
   PubMed Web of Science ®Google Scholar
• Mphahlele MJ, Paumo HK, Rhyman L, Ramasami P. Synthesis and photophysical properties of polycarbo-substituted quinazolines derived from the 2-aryl-4-chloro-6-iodoquinazolines. Molecules 2015;20:14656–83.
   PubMed Web of Science ®Google Scholar
• Khansole SV, Mokle SS, Sayyed MA, Vibhute YB. Pyridinium iodochloride: an efficient reagent for iodination of hydroxylated aromatic ketones and aldehydes. J Chinese Chem Soc 2008;55:871–4.
   Web of Science ®Google Scholar
• Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 1983;65:55–63.
   PubMed Web of Science ®Google Scholar
• Stamos J, Sliwkowski MX, Eigenbrot C. Structure of the epidermal growth factor receptor kinase domain alone and in complex with a 4-anilinoquinazoline inhibitor. J Biol Chem 2002;10:46265–72.
   Web of Science ®Google Scholar
• Morris GM, Huey R, Lindstrom W, et al. AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility. J Comput Chem 2009;30:2785–91.
   PubMed Web of Science ®Google Scholar
• Arcadi A, Blesi F, Cacchi S, et al. 2,5,7-Trisubstituted benzo[b]furans through a copper- and/or palladium-catalyzed assembly and functionalization process. Tetrahedron Lett 2011;52:5149–52.
   Web of Science ®Google Scholar
• See CCDC 1815109 at https://www.ccdc.cam.ac.uk/Community/Depositastructure. [last accessed 6 Jan 2018].
   Google Scholar
• Trivedi AB, Kitabatake N, Doi E. Toxicity of dimethyl sulfoxide as a solvent in bioassay system with HeLa cells evaluated colorimetrically with 3-(4,5-dimethyl thiazol-2-yl)-2,5-diphenyl-tetrazolium bromide. Agric Biol Chem 1990;54:2961–6.
   PubMedGoogle Scholar
• Da Violante G, Zerrouk N, Richard I, et al. Evaluation of the cytotoxicity effect of dimethyl sulfoxide (DMSO) on Caco2/TC7 colon tumor cell cultures. Biol Pharm Bull 2002;25:1600–3.
   PubMed Web of Science ®Google Scholar
• Hirata A, Hosoi F, Miyagawa M, et al. Sensitivity to gefitinib (Iressa, ZD1839) in non-small cell lung cancer cell lines correlates with dependence on the epidermal growth factor (EGF) receptor/extracellular signal-regulated kinase 1/2 and EGF receptor/Akt pathway for proliferation. Mol Cancer Ther 2005;65:4253–472.
   Google Scholar
• Lemos C, Kathmann I, Giovannetti E, et al. Impact of cellular folate status and epidermal growth factor receptor expression on BCRP/ABCG2-mediated resistance to gefitinib and erlotinib. British J Cancer 2009;100:1120–7.
   PubMed Web of Science ®Google Scholar
• Leroux FR, Manteau B, Vors J-P, Pazenok S. Trifluoromethyl ethers – synthesis and properties of an unusual substituent. Beilstein J Org Chem 2008;4:1–15.
   PubMed Web of Science ®Google Scholar
• Sirisoma N, Pervin A, Zhang H, et al. Discovery of N-(4-methoxyphenyl)-N,2-dimethylquinazolin-4-amine, a potent apoptosis inducer and efficacious anticancer agent with high blood brain barrier penetration. J Med Chem 2009;52:2341–51.
   PubMed Web of Science ®Google Scholar
• Coskun D, Erkisa M, Ulukaya E, et al. Novel 1-(7-ethoxy-1-benzofuran-2-yl) substituted chalcone derivatives: synthesis, characterization and anticancer activity. Eur J Med Chem 2017;136:212–22.
   PubMed Web of Science ®Google Scholar
• Schwartz SM, Bennett MR. Death by any other name. Am. J. Pathol 1995;147:229–34.
   PubMed Web of Science ®Google Scholar
• Fink SL, Cookson BT, Apoptosis p. necrosis Apoptosis, pyroptosis, and necrosis: mechanistic description of dead and dying eukaryotic cells. Infect Immun 2005;73:1907–16.
   PubMed Web of Science ®Google Scholar
• Lauber K, Blumenthal SG, Waibel M, Wesselborg S. Clearance of apoptotic cells: getting rid of the corpses. Mol Cell 2004;14:277–87.
   PubMed Web of Science ®Google Scholar
• Taylor RC, Cullen SP, Martin SJ. Apoptosis: controlled demolition at the cellular level. Nat. Rev. Mol. Cell Biol 2008;9:231–41.
   PubMed Web of Science ®Google Scholar
• Fischer U, Janicke RU, Schulze-Osthoff K. Many cuts to ruin: a comprehensive update of caspase substrates. Cell Death Differ 2003;10:76–100.
   PubMed Web of Science ®Google Scholar
• Hopfner M, Sutter AP, Huether A, et al. Targeting the epidermal growth factor receptor by gefitinib for treatment of hepatocellular carcinoma. J Hepatol 2004;41:1008–16.
   PubMed Web of Science ®Google Scholar
• Schiffer E, Housset C, Cacheux W, et al. Gefitinib, an EGFR inhibitor, prevents hepatocellular carcinoma development in the rat liver with cirrhosis. Hepatology 2005;41:307–14.
   PubMed Web of Science ®Google Scholar
• Arteaga CL. Epidermal growth factor receptor dependence in human tumors: more than just expression? Oncologist 2002;7:31–9.
   PubMed Web of Science ®Google Scholar