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Design, Synthesis, and Molecular Docking Studies of 2‐(Furan‐2‐yl)quinazolin‐4‐one Derivatives as Potential Antiproliferative Agents

Fifteen new derivatives of quinazolin‐4‐one bearing the 2‐furyl moiety at position 2 and a substituted phenyl moiety at position 3 were designed and synthesized to be evaluated as cytotoxic agents. Their chemical structures were confirmed by spectral and elemental analysis; cytotoxic activity evaluation was performed against HEPG2, HCT116, and MCF7 cancer cell lines using the sulforhodamine‐B assay. All the tested compounds except 6a showed high potency against the HEPG2 cancer cell line (IC50 8–101  nM/mL); 11 compounds out of 15 proved to be potent against HCT116 cells (IC50 3–49 nM/mL), also 11 of the tested compounds showed high potency against MCF7 cells with IC50 values ranging from 7 to 63 nM/mL. The rest of the tested compounds showed IC50 values of more than 100 nM/mL. Compounds 3e and 4d are the most active compounds against HEPG2 cells; in addition, 3e is the most active compound against MCF7 cells. Also, compounds 4a, 3a, and 3b are the most active compounds against HCT116 cells. Compounds 3a, 3b, 3e, 4a, and 4d were also evaluated for their inhibitory activity against the EGFR tyrosine kinase (EGFR‐TK) and showed a percentage inhibitory activity ranging from 53 to 84%. The most potent EGFR‐TK inhibitors, 3a (84%), 3b (75%), and 3e (60%), were docked into the ATP binding site of the EGFR to explore their binding mode and possible interactions.