Synthesis, characterization, anti-proliferative activity and DFT study of 1H-benzo[f]chromene-2-carbothioamide derivatives.

• Tricyclic 1 H -benzo[ f ]chromene-2-carbothioamides were synthesized as potential anticancer agents. • The cytotoxic activity was tested against MCF-7, HepG-2 and PC-3 cell lines. • Various molecular descriptors, frontier molecular orbitals, Mulliken analysis and electronic properties were studied. • The energy gaps, reactivity descriptors values and molecular docking of the target compounds were discuses. Reaction of 7‑methoxy-2-naphthol with appropriate aromatic aldehydes and 2-cyano-ethanethioamide provided the corresponding 3-amino-1-aryl-9‑methoxy-1 H -benzo[ f ]chromene-2-carbothioamide. The structures of these compounds were established on the basis of IR, 1H NMR, 13C NMR, MS data and elemental analysis. Furthermore, the anti-proliferative properties were evaluated against the human cancer cell lines MCF-7, HepG-2 and PC-3 in comparison to the positive controls Vinblastine and Doxorubicin, employing the viability assay. The obtained results confirmed that some of the tested molecules revealed strong and selective cytotoxic activities against the three cancer cell lines. Moreover, various molecular descriptors, frontier molecular orbitals (FMO), Mulliken analysis and electronic properties were studied to probe the biological activity behavior of the synthesized 1 H -benzo[ f ]chromene-2-carbothioamide derivatives. The effect of electron withdrawing groups (EWGs) and electron donating groups (EDGs) was also explored on the structural parameters and electronic nature of compounds. The energy gaps, reactivity descriptors values and molecular docking studies exhibited that some 1 H -benzo[ f ]chromene-2-carbothioamide derivatives would be active biological compounds. [ABSTRACT FROM AUTHOR]