A variety of amines have been employed to functionalize isobenzofuran-1,3-dione to obtain isoindoline-1,3-dione derivatives in the base free conditions. All the synthesized compounds are screened for their bioactivity through molecular docking, cytotoxicity (against HeLa) and antioxidant activity. ABTS and DPPH are employed to assess the antioxidant activity. Among the synthesized isoindoline-1,3-dione derivatives (3a-k), compound 3e has showed the best antioxidant activity and also exhibited better binding energy when docked with caspase-3 protein. Cytotoxicity of the synthesized compounds was studied against cervical cancer cell line (HeLa) and compound 3e has displayed better activity than other isoindoline derivatives.