A series of naphthalene based hybrid heterocyclics were designed and synthesized by the replacement of benzene ring with napthalene on 4-substituted 4H-chromenes. As a part of our continuous efforts in accessing the bioactive compounds by using simple techniques, we report the synthesis of azolidinedione/thiazolidinediones tethered 4-substituted benzo[f] chromene derivatives under greener reaction conditions and in silico evaluation of anticancer activity. Docking studies showed that the synthesized compounds exhibit good predicted binding affinities at the colchicine binding site of tubulin (Figure 1).