3,3-Benzene-1,4-diylbis(1-phenylprop-2-enone) 3 reacted with 2-cyanoethanethioamide 4 to afford the corresponding 4,4-benzene-1,4-diylbis(6-phenyl-2-thioxo-1,2-dihydropyridine-3-carbonitrile) 5. The synthetic potentiality of compound 5 was investigated in the present study via its reactions with several active-hydrogen containing compounds 6a-f aiming to synthesize 4,4-(1,4-phenylene)bis(3-amino-6-phenylthieno[2,3-b]pyridine) derivatives 8a-h directly in case of 8d,e,f,h and via 2,2-{1,4-Phenylenebis[(3-cyano-6-phenylpyridine-4,2- diyl)thio]} derivatives 7a-c,g in case of 8a-c,g. The structures of all the newly synthesized heterocyclic compounds were elucidated by considering the data of IR, 1 H NMR, mass spectra as well as that of elemental analyses. Anti-cancer activities for all the newly synthesized heterocyclic compounds were investigated.