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 1H NMR, 13C 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 µM, when compared with the standard inhibitor (i.e., thiourea having IC50 value 21.8 ± 1.51 µM). 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.