novel series of 4,4'-(1,4-phenylene)bis(3-chloro-1-azetidin-2-one) (11-20) and 4,4'-(1,3-phenylene)bis(4- methoxyphenylazetidin-2-one) (23, 26) along with azetidinone-Schiff base hybrids (22, 25) were synthesized from the Staudinger ketene-imine cyclo addition reaction of the Schiff base dimers and the acetylchlorides. All the prepared compounds were screened for their antibacterial activity against nine different strains and anticancer activity against three cell lines including HeLa, MDA-MB-231 and ACHN. Many compounds showed good antibacterial activity. Particularly azetidinone-Schiff base hybrids showed remarkable antibacterial activity against six strains. (3S, 4S)-3-chloro-4-(4-((2R, 3R)-3-chloro-4-oxo-1-p-toylazetidin-2-yl)phenyl)-1-p-toylazetidin-2-one (12) and (3S, 4S)-3-chloro-4-(3-((2R, 3R)-3-chloro-4-oxo-1-p-toylazetidin-2-yl)phenyl)-1-p-toylazetidin-2-one (17) exhibited potent anticancer activity withthe IC50 values of (HeLa, 0.41; MDA-MB-231 0.42; ACHN, 0.45) and (HeLa, 0.46; MDA-MB-231, 0.40; ACHN, 0.48) respectively.