Synthesis, characterization, oxidative degradation, antibacterial activity and acetylcholinesterase/butyrylcholinesterase inhibitory effects of some new phosphorus(V) hydrazides

Some new phosphorus(V) hydrazides 1a–12a were synthesized and characterized by 1H, 13C, 31P NMR, IR spectroscopy and elemental analysis. Moreover, the interaction of Cu(M)2·nH2O with 1a, 3a and 7a gave 4,4′-bis(morpholine)diazene (1b). In fact, in these reactions, copper(II) ions acted as oxidizing agent. The results supported the proposed mechanism. The structures of compounds 1a, 1b and 1c were further determined by X-ray crystallography. Compounds 1a–12a were screened for their antibacterial activities. Also, the acetyl- and butyrylcholinesterase inhibitory activity of 1a, 3a, 7a, 11a and 12a was measured using Ellman’s method. It is interesting that these compounds were more potent inhibitors of BChE than of AChE. Also, using Lineweaver–Burk plots, it was indicated these compounds are mixed inhibitors.

Graphical abstract12 New phosphorus(V) hydrazides were synthesized and evaluated with their antibacterial and cholinesterase inhibition activities. The reaction of 1a, 3a and 7a with solution of Cu(M)2·nH2O was studied.Figure optionsDownload full-size imageDownload as PowerPoint slide