Covalent epidermal growth factor receptor (EGFR) inhibitors in targeted therapy of drug-resistant non-small cell lung cancer

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Non-small cell lung cancer (NSCLC) is the main subtype of lung cancer and is a common cause of cancer-related mortality worldwide. Mutations in the epidermal growth factor receptor (EGFR) gene play a leading role in the pathogenesis of NSCLC, causing its pathological activity. The first generation of EGFR inhibitors, acting reversibly, effectively block the effects of EGFR with activating mutations by benefiting from competition with adenosine triphosphate for binding to the kinase. However, after several months of treatment, a secondary T790M mutation often occurs, causing resistance to subsequent therapy with these drugs. Effective inhibition of EGFR with the T790M mutation was possible due to second-generation inhibitors acting via a covalent mechanism. However, the second generation of covalent inhibitors has received limited use in therapy due to insufficient selectivity for EGFR T790M and a narrow therapeutic window. The discovery of covalent pyrimidine-based inhibitors has led to the emergence of a number of effective and safer third-generation drugs for the treatment of NSCLC with the EGFR T790M mutation. This review contains a brief description of first- and second-generation EGFR inhibitors and a detailed discussion of the main stages in the development of third-generation inhibitors. The main emphasis is placed on the identified “structure–activity” patterns. Data are provided on inhibitors that have received the status of approved drugs for the treatment of NSCLC. Promising directions for the development of novel EGFR inhibitors are indicated.

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A. Shvetsov

National Research Ogarev Mordovia State University

编辑信件的主要联系方式.
Email: shvetsov.1984@list.ru
俄罗斯联邦, ul. Bolshevistskaya 68, Saransk, 430005

A. Semenov

National Research Ogarev Mordovia State University

Email: shvetsov.1984@list.ru
俄罗斯联邦, ul. Bolshevistskaya 68, Saransk, 430005

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2. Fig. 1. (a) – First-generation EGFR inhibitors; (b) – structure of the ATP-binding site of EGFR [9]; (c) – mode of binding of erlotinib to EGFR [9].

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3. Fig. 2. Second-generation EGFR inhibitors.

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4. Fig. 3. (a) – First third-generation EGFR inhibitors; (b) – mode of WZ4002 binding to EGFR; (c) – superposition of WZ4002 and rociletinib superpositions in EGFR T790M [30].

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5. Fig. 4. Limertinib and pyridine analogs of osimertinib.

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6. Fig. 5. Pyrazole- and triazole-containing analogs of osimertinib.

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7. Fig. 6. Dual-action inhibitors of EGFR DM/ALK and EGFR DM/BTK.

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8. Fig. 7. Pyrrole-, pyrazole-pyrimidine and purine EGFR DM inhibitors.

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9. Fig. 8. Thiopheno- and thiopyranopyrimidine EGFR inhibitors DM.

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10. Fig. 9. EGFR DM inhibitors with quinazoline and modified quinazoline scaffolds.

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11. Scheme 1. Osimertinib precursors and its major metabolites.

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12. Scheme 2. 5-Methylthio analogues of WZ4002.

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13. Scheme 3. Analogues of WZ4002 with urea as a linker insert.

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14. Scheme 4. Rociletinib analogues.

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15. Scheme 5. Rociletinib analogues.

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16. Scheme 6. 2,4-Diaminopyrimidine analogs of osimertinib.

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17. Scheme 7. N-Oxide and fluorinated analogs of osimertinib.

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18. Scheme 8. Osimertinib analogues.

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19. Scheme 9. Cyclopropyl analogs of osimertinib.

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20. Scheme 10. Dosimertinib and its precursors.

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21. Scheme 11. Osimertinib analogues.

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22. Scheme 12. Osimertinib analogues.

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23. Scheme 13. Pyrazole- and triazole-containing 2,4-diaminopyrimidines.

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24. Scheme 14. Modifications of the “head” and amine parts of osimertinib.

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25. Scheme 15. Osimertinib analogs with a pyridine linker.

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26. Scheme 16. Tetrahydrothienopyridine analogs of osimertinib.

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27. Scheme 17. Modifications of acrylamide and pyrimidine backbone.

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28. Scheme 18. Allenamide analogs of osimertinib.

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29. Scheme 19. Furanopyrimidine EGFR inhibitors DM.

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