Novel hydrazonoyl halides 3, 5 and bis-hydrazonoyl halides 7, 9 were synthesized. The synthetic utility of bis-hydrazonoyl halide 7 was explored to prepare novel bis-azole 13 with antipyrine moiety. On the other hand, [1,3,4]thiadiazol-2(3H)-ylidene 17 and thiazol-2(3H)-ylidene 21 derivatives, with antipyrine moiety, were prepared from the reaction of 3-mercapto-3-(phenylamino)acrylamide derivative 10 with N-phenyl benzenecarbohydrazonoyl chloride (14) and 3-(2-bromoacetyl)-2H-chromen-2-one (18), respectively. The structures of the isolated products were confirmed by spectral data (IR, (1)H-NMR, (13)C-NMR, MS) and elemental analyses. The anti-cancer activitiy of the synthesized products against the colon carcinoma (HCT) cell line was determined and the results revealed promising activity of compound 3. In addition, the antimicrobial activity of some selected products was evaluated. The results proclaimed that compounds 9, 17, and 21 have high antibacterial activity against Gram-positive bacteria (SA, BS) and Gram-negative bacteria (PA, EC).