A quantitative structure activity relationship study was performed on a series of 4-flouro-2- cyanopyrrolidine derivatives possessing Dipeptidyl Peptidase IV (DPP IV) inhibitory activity for establishing quantitative relationship between biological activity and their physicochemical / structural properties. Several statistical regression expressions were obtained using stepwise multiple linear regression (MLR), partial least squares regression (PLSR), partial component regression (PCR) analysis. Three statistical significant models were generated (r2 = 0.830, 0.893, 0.875 for model 1, 2 and 3 respectively) indicating that biological activity is influenced by the descriptors, T_C_N_6, T_C_N_3, MMFF_8, slogp etc.