Catalyst free new bioactive 2‐amino‐4‐(2‐oxo‐2H‐chromen‐4‐yl)‐6‐arylpyridine‐3‐carbonitrile molecular entities (2 a‐2 o) have been synthesized from 4‐formylcoumarins with malononitrile, different ketones and ammonium acetate via one‐pot four component coupling reaction under neat microwave method. Detailed characterization of all the compounds and anticancer properties for the synthesized compounds are reported. Compounds 2 f and 2 k exhibited promising anticancer activity at low concentration (10−5 M) against NCI‐60 cell lines. Further, IC50 values were calculated for most potent compounds against three cancer cell lines such as HT‐29, Hep‐G2 and KB. Among the eight compounds, 2 f and 2 k are exhibited most promising activity, the potent anticancer molecules 2 f and 2 k were screened for their CT‐DNA cleavage and fluorescence quenching study with transport protein BSA. Molecular docking study has been performed for the synthesized compounds with binding site of the tubulin using podophyllotoxin‐tubulin stathmin‐like domain complex (PDB 1SA1) and results obtained are quite good.

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New coumarin‐benzimidazole hybrids (3a–f) have been synthesized from 4‐formylcoumarins and a series of N‐sulphonation (4 a‐f) and N‐methylation (5 a‐f) compounds were obtained from compounds (3a–f). All the synthesized compounds have exhibited good antimicrobial activity. Docking studies provide valuable insights to potential binding modes of inhibitors. Anti cancer activity of compound 4 a and 4 c have shown excellent activity against HeLa cell line. Whereas compound 4 a and 4 d exhibited higher activity against HT 29 cell lines. We calculated the LC50, TGI and GI50 which show < 10 mg/mL. The synthesized compounds were characterized by IR, NMR, Mass spectral analysis and few of them by single X‐ray crystallography analysis.