A new series of phenoxyacetic acid bearing pyrazoline derivatives 7a–k were synthesized and characterized by IR, 1 H-NMR, and mass spectral data. The investigated compounds were screened for their diuretic activity by standard Lipschitz method. Furthermore, the series under investigation were assessed for their drug-likeness by suitable software programs. These compounds were found to have promising results against a given set of diuretic parameters, i.e., cumulative urine output, diuretic activity, diuretic action, and Lipchitz values. Nevertheless, compounds 7d, 7h, 7i, and 7k bearing electron withdrawing group (Cl-) showed pronounced diuretic propensity than the standard furosemide.