Synthesis, characterization and anticancer evaluation of new 1H-naphtho[2,3-d]imidazole-4,9-dione-1,2,4-oxadiazole hybrids
Keywords:Oxadiazole, anticancer activity, Molecular docking, Imidazole, hybrid molecules, heterocyclic compounds, medicinal chemistry
New series of 1H-naphtho[2,3-d]imidazole-4,9-dione-1,2,4 oxadiazoles (10a-10l) synthesized using NH2OH.HCl/Et3N and POCl3/DMF (Vilsmeier reagent) mediated one-pot reaction between 2-(4,9-dioxo-4,9-dihydro-1H-naphtho[2,3-d]imidazol-1-yl)acetonitrile and several aromatic carboxylic acids as key approach have been reported here. All synthesized compounds were screened for the in vitro cytotoxicity against three human cancer cell lines such as A549, PC3, and MCF-7. Three compounds (10d, 10f and 10k) exhibited superior activity than the standard etoposide against all the cell lines with IC50 values <2 μM. Finally, molecular docking studies revealed the important binding interactions of potent compounds 10d, 10f and 10k with the α, β-tubulin (PDB ID-1SA0).