Pyrrolizine/pyrrolidine scaffolds have long been described for their encouraging biological responses such as anti-cancer, anti-microbial, anti-viral, etc. Hydantoin, a versatile pharmacophore, has also been employed for developing a variety of bioactive molecules. Therefore, we anticipated to integrate these two privileged moieties into a single one for enriched biological applications. In this work, we developed an effective synthesis of Dispiroimidazolidine Pyrrolizine/pyrrolidine conjugates via 1, 3-cycloaddition reaction of azomethine ylides generated in situ by the 8-bromotryptanthrin and Acyclic/Cyclic α-amino acid with the Knoevenagel adduct derivatives (derived from the reaction of Hydantoin with substituted benzaldehydes) We further evaluated anti-bacterial, anti-fungal and cytotoxicity activity of all the compounds against MCF-7 human breast cancer cells. Compound 3A-1 & 2, 3 B-1 & 2 and 3 A-9 & B-9 containing 4-flouro and nitro substituent on Phenyl ring and furyl with Bromo atom on Indolo[2,1-b]quinazoline-6,12-dione nucleus showed better activity having IC values 1.82 μg/ml,1.94 μg/ml & 1.88 μg/ml respectively.