Cyclin Dependent Kinase 4(CDK4) is responsible for the progression of cell cycle at G1-S phase. CDK inhibitor alters the cell cycle that will inhibit cancer cell formation. Spirooxindole derivative targets p53-MDM2 interaction that inhibits CDK4 protein which results in inhibition of cell cycle. Spirooxindole is a unique three- dimensional scaffold that was first isolated from Rubiaceae and Apocynaceae plants. Spriooxindole is a promising drug through many years which can be used to treat an array of diseases such as cancer, analgesic, mental disorder, bacterial and viral infection. From past decade spirooxindole became a huge topic of interest in bio medicinal field due to its multipotentability. In our present work, we have performed QSAR (Quantitative Structure-Activity Relationship) and Molecular modeling studies on a series of chiral tetrahydronaphthalene-fused spirooxindole, resulting in a cross validated r2cv value of 0.858 obtained by Leave one out method (LOO), and predicted r2pred.0.622 with coefficient of correlation of (r) that was obtained by the multiple regression analysis is0.949.A series of new compounds were designed based upon the generated QSAR model. Afterwards these compounds were docked with the protein and checked for their ADME properties. Toxicity of the new compounds was also predicted.