A series of new hydrazone derivatives were synthesized using dicyclopropyl ketone as starting material. Unexpected reaction of salicylaldehyde with (dicyclopropylmethylene)hydrazine yielded the appropriate bis(salicylaldehyde azine). Treatment of the (dicyclopropylmethylene)hydrazine with the appropriate coupling agents gave the corresponding imides, imidazolones, oxazolones, quinazolinones and triazoles, respectively. The synthesized compounds were characterized using IR, 1H-NMR, 13C-NMR and mass spectral data. These newly formed products were tested for their antibacterial and antifungal activities and most of the compounds showed high activity compared with Ciprofloxacin as positive controls. In addition, the compounds were also, examined for their anticancer activities against breast cancer cell line (MCF7) compared with cisplatin as a positive control. The novel synthesized compounds showed satisfactory activity against (MCF7) with mean IC50 values ranging from 21.5 to 100 μM.