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Herein, we describe new quinazoline and tetrahydropyridothieno[2,3-d]pyrimidine derivatives with an acrylamido group at positions 6 and 7 respectively, and with variable anilino, sulfonamido and cycloalkylamino substituents at position 4. The lipophilic and steric properties of the position 4 substituent seem crucial for activity. Several compounds were more active than gefitinib in inhibiting the wild type EGFR enzyme, the autophosphorylation of the mutant EGFR expressing cell line (H1975), and the growth of cell lines with wild type and mutant EGFR tyrosine kinase. Moreover, a novel synthesis of the quinazoline nucleus from a formimidate derivative is described.

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Quinazoline and tetrahydropyridothieno[2,3-d]pyrimidine derivatives as irreversible EGFR tyrosine kinase inhibitors: influence of the position 4 substituent