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Graphical abstract Highlights • Fifteen new 4-anilinoquinazoline-substituted triazole hybrid compounds were designed and synthesized. • Their anticancer activities against human cancer cell lines were evaluated. • Compound 13a exhibited up to 100-fold higher cytotoxicity in comparison with erlotinib. • Molecular docking suggests greater affinity of 13a-b and 14c than erlotinib for the ATP binding sites of the active and inactive conformations of EGFR. Abstract In this research several series of novel dioxygenated ring fused 4-anilinoquinazolines (10a-d) and 4-anilinoquinazoline-substituted triazole hybrid compounds (11 – 14) have been designed and synthesized. Their biological significance was highlighted by evaluating in vitro for anticancer activities, wherein several compounds displayed excellent activity specifically against three human cancer cell lines (KB, epidermoid carcinoma; HepG2, hepatoma carcinoma; SK-Lu-1, non-small lung cancer). Especially, compound 13a exhibited up to 100-fold higher cytotoxicity in comparison with erlotinib. Docking the most cytotoxic compounds (11d , 13a , 13b , and 14c) into the ATP binding site of different EGFR tyrosine kinase domains was perfomed to predict the analogous binding mode of these compounds to the EGFR targets. [ABSTRACT FROM AUTHOR]

[Display omitted] • Multicomponent synthesis of novel naphthoquinone-chalcone hybrids was shown. • The reaction was performed under mild and metal-free condition. • The plausible mechanisms for the formation of compounds 7a-m , 24a-c were discussed. A facile and efficient synthesis of novel naphthoquinone-based chalcone hybrids (7 and 24) via the microwave-assisted one-pot three-component reactions of 2-substituted-1,4-naphthoquinones, N , N -dimethylformamide dimethyl acetal (DMF-DMA), and acetophenone derivatives has been reported. Whereas the synthesis of hybrids 7 proceeded via a condensation, 1,4-addition, rotation, elimination, and [1,3]-H shift sequence of steps, the synthesis of hybrids 24 were formed through a three-step sequence including condensation, 1,4-addition, and elimination reactions. [ABSTRACT FROM AUTHOR]