Synthesis, urease inhibition screening and molecular docking studies of piperonal based imine derivatives

A series of piperonal-based imines (3a-c) and bis-imines (5a-o) have been synthesized in search of new urease inhibitors. Synthesized compounds were characterized by H-1 NMR, C-13 NMR and EI-MS. These derivatives were subjected to evaluation of urease inhibitory potential, which exhibited a varied degree of potential, ranging from 41.7 +/- 5.8 to 353.6 +/- 5.8 mu M, when compared with the standard inhibitor (i.e., thiourea having IC50 value 21.8 +/- 1.51 mu M). Amongst the synthesized bis-imines, three compounds 5d, 5h, and 5g exhibited good inhibitory potential having IC50 values 41.7 +/- 5.8, 43.7 +/- 5.8, and 52.6 +/- 5.8 respectively so can be further investigated. The remaining compounds exhibited moderate to weak activities. Molecular modeling studies were performed to understand the binding interactions with the enzyme.