In continuation with our earlier work on MAO inhibitory curcumin based pyrazoline analogues, we synthesized a series of pyrazoline derivatives (from vanilylidene acetophenone). The compounds were evaluated for their hMAO inhibitory potential and also for their intestinal permeability and metabolic stability characteristics. Activity profile of the compounds was found to be similar to the earlier() reported series. The potent hMAO-A (compound 6; Ki=0.10 +/- 0.01 mu M, SI=3.08x10(-6)), hMAO-B (compound 2; Ki=0.55 +/- 0.03 mu M, SI=13.13) and non-selective (compound 13; Ki=1.36 +/- 0.10 mu M) inhibitors were found to have better permeability and metabolic stability characteristics in comparison with curcumin. Molecular docking simulation was performed to see any difference in orientation of potent compounds in the current series with the earlier reported one in hMAO active site.