Dipeptidyl Peptidase-IV (DPP-IV) was found to be one of the emerging targets in the field of antidiabetic drug development. In recent years, Piperidone analogs have shown their application in the field of diabetology as observed in the crystallographic structure of DPP-IV. All the ligand molecules were designed considering the pharmacophoric features of the GGO901 (Co-crystallised ligand of DPP-IV with the PDB entry-2OQI). It was thought worthwhile to perform docking study by extracting the crystallographic structure of Dipeptidyl Peptidase-IV inhibitor with all the virtually developed molecules to ensure the better binding energy which would be well able to explain the ligand target interaction of novel piperidone analogs, actively inhibiting DPP-IV enzyme. Based on the docking output, a few novel imidazole linked piperidone analogs were synthesized & as a part of the structure elucidation process various spectroscopic data were collected and subsequently analysed. All the analytically proven synthesized compounds were further sent for biological evaluation.