Design, synthesis, and biological evaluation of pyrido[2,3-d]pyrimidine and thieno[2,3-d]pyrimidine derivatives as novel EGFR^L858R/T790M inhibitors

References

• da Cunha Santos G, Shepherd FA, Tsao MS. EGFR mutations and lung cancer. Annu Rev Pathol. 2011;6:49–69.
   PubMed Web of Science ®Google Scholar
• Cheng WL, Feng PH, Lee KY, Chen KY, Sun WL, Van Hiep N, Luo CS, Wu SM. The role of EREG/EGFR pathway in tumor progression. Int J Mol Sci. 2021;22:12828.
   PubMedGoogle Scholar
• Sabbah DA, Hajjo R, Sweidan K. Review on epidermal growth factor receptor (EGFR) Structure, signaling pathways, interactions, and recent updates of EGFR inhibitors. Curr Top Med Chem. 2020;20(10):815–834.
   PubMed Web of Science ®Google Scholar
• Wang J, Wang B, Chu H, Yao Y. Intrinsic resistance to EGFR tyrosine kinase inhibitors in advanced non-small-cell lung cancer with activating EGFR mutations. Onco Targets Ther. 2016;9:3711–3726.
   PubMed Web of Science ®Google Scholar
• Muhsin M, Graham J, Kirkpatrick P. Gefitinib. Nat Rev Drug Discov. 2003;2(7):515–516.
   PubMed Web of Science ®Google Scholar
• Hida T, Ogawa S, Park JC, Park JY, Shimizu J, Horio Y, Yoshida K. Gefitinib for the treatment of non-small-cell lung cancer. Expert Rev Anticancer Ther. 2009;9(1):17–35.
   PubMed Web of Science ®Google Scholar
• Brower JV, Robins HI. Erlotinib for the treatment of brain metastases in non-small cell lung cancer. Expert Opin Pharmacother. 2016;17(7):1013–1021.
   PubMed Web of Science ®Google Scholar
• Abdelgalil AA, Al-Kahtani HM, Al-Jenoobi FI. Erlotinib. Profiles Drug Subst Excip Relat Methodol. 2020;45:93–117.
   PubMedGoogle Scholar
• Tagliamento M, Genova C, Rijavec E, Rossi G, Biello F, Dal Bello MG, Alama A, Coco S, Boccardo S, Grossi F. Afatinib and Erlotinib in the treatment of squamous-cell lung cancer. Expert Opin Pharmacother. 2018;19(18):2055–2062.
   PubMed Web of Science ®Google Scholar
• Yang JC, Schuler M, Popat S, Miura S, Heeke S, Park K, Marten A, Kim ES. Afatinib for the treatment of non-small cell lung cancer harboring uncommon EGFR mutations: a database of 693 cases. J Thorac Oncol. 2020;15(5):803–815.
   PubMed Web of Science ®Google Scholar
• Harvey RD, Adams VR, Beardslee T, Medina P. Afatinib for the treatment of EGFR mutation-positive NSCLC: a review of clinical findings. J Oncol Pharm Pract. 2020;26(6):1461–1474.
   PubMed Web of Science ®Google Scholar
• Sakuma Y, Yamazaki Y, Nakamura Y, Yoshihara M, Matsukuma S, Nakayama H, Yokose T, Kameda Y, Koizume S, Miyagi Y. WZ4002, a third-generation EGFR inhibitor, can overcome anoikis resistance in EGFR-mutant lung adenocarcinomas more efficiently than Src inhibitors. Lab Invest. 2012;92(3):371–383.
   PubMed Web of Science ®Google Scholar
• Zhou W, Ercan D, Chen L, Yun CH, Li D, Capelletti M, Cortot AB, Chirieac L, Iacob RE, Padera R, et al. Novel mutant-selective EGFR kinase inhibitors against EGFR T790M. Nature. 2009;462(7276):1070–1074.
   PubMed Web of Science ®Google Scholar
• Jia Y, Juarez J, Li J, Manuia M, Niederst MJ, Tompkins C, Timple N, Vaillancourt M-T, Pferdekamper AC, Lockerman EL, et al. EGF816 exerts anticancer effects in non–small cell lung cancer by irreversibly and selectively targeting primary and acquired activating mutations in the EGF receptor. Cancer Res. 2016;76(6):1591–1602.
   PubMed Web of Science ®Google Scholar
• Walter AO, Sjin RTT, Haringsma HJ, Ohashi K, Sun J, Lee K, Dubrovskiy A, Labenski M, Zhu Z, Wang Z, et al. Discovery of a mutant-selective covalent inhibitor of EGFR that overcomes T790M-mediated resistance in NSCLC. Cancer Discov. 2013;3(12):1404–1415.
   PubMed Web of Science ®Google Scholar
• Cross DA, Ashton SE, Ghiorghiu S, Eberlein C, Nebhan CA, Spitzler PJ, Orme JP, Finlay MR, Ward RA, Mellor MJ, et al. AZD9291, an irreversible EGFR TKI, overcomes T790M-mediated resistance to EGFR inhibitors in lung cancer. Cancer Discov. 2014;4(9):1046–1061.
   PubMed Web of Science ®Google Scholar
• Park K, Jӓnne PA, Kim DW, Han JY, Wu MF, Lee JS, Kang JH, Lee DH, Cho BC, Yu CJ, et al. Olmutinib in T790M-positive non-small cell lung cancer after failure of first-line epidermal growth factor receptor-tyrosine kinase inhibitor therapy: a global, phase 2 study. Cancer. 2021;127(9):1407–1416.
   PubMed Web of Science ®Google Scholar
• Kim ES. Olmutinib: first global approval. Drugs. 2016;76(11):1153–1157.
   PubMed Web of Science ®Google Scholar
• He J, Huang Z, Han L, Gong Y, Xie C. Mechanisms and management of 3rd-generation EGFR-TKI resistance in advanced non-small cell lung cancer. Int J Oncol. 2021;59(5):90.
   PubMed Web of Science ®Google Scholar
• Zhang W, Fan YF, Cai CY, Wang JQ, Teng QX, Lei ZN, Zeng L, Gupta P, Chen ZS. Olmutinib (BI1482694/HM61713), a novel epidermal growth factor receptor tyrosine kinase inhibitor, reverses ABCG2-mediated multidrug resistance in cancer cells. Front Pharmacol. 2018;9:1097.
   PubMed Web of Science ®Google Scholar
• Huang X, Cheng CC, Fischmann TO, Duca JS, Richards M, Reddy PK, Tadikonda PA, Zhao L, Siddiqui MA, Parry D, et al. Structure-based design and optimization of 2-aminothiazole-4-carboxamide as a new class of CHK1 inhibitors. Bioorg Med Chem Lett. 2013;23(9):2590–2594.
   PubMed Web of Science ®Google Scholar
• Darandale SN, Mulla NA, Pansare DN, Sangshetti JN, Shinde DB. A novel amalgamation of 1,2,3-triazoles, piperidines and thieno pyridine rings and evaluation of their antifungal activity. Eur J Med Chem. 2013;65:527–532.
   PubMed Web of Science ®Google Scholar
• Wang SB, Deng XQ, Zheng Y, Yuan YP, Quan ZS, Guan LP. Synthesis and evaluation of anticonvulsant and antidepressant activities of 5-alkoxytetrazolo[1,5-c]thieno[2,3-e]pyrimidine derivatives. Eur J Med Chem. 2012;56:139–144.
   PubMed Web of Science ®Google Scholar