A variety of novel 3°-amine consisting 5-acetyl-6-chloroindolin-2-one analogues(8a-e) were developed and synthesized by reacting of 6-chloro-5-(2-chloroacetyl)-indolin-2-one and substituted secondary aminesin the presence of a Tetrabutylammonium bromide as a catalyst. The biological activity of these derivatives was investigated, and the bio-assay revealed that the compounds have moderate to good antioxidant properties. Notably, 8a and 8d compounds possessed high antioxidant activitywhich is revealed by DPPH method. Furthermore, molecular docking investigations were carried out to better understand how these compounds interact with the Human Superoxide Dismutase enzyme (SOD-1).Among the molecules, 8a and 8d have highest binding score (-9.6 kcal/mol) towards Human Superoxide Dismutase enzyme (SOD-1). Ligand 8a has strong binding affinity at binding site of enzyme with strong Hydrogen bonding with His-D-110, and ASP-I-76.