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SYNTHESIS, CHARACTERIZATION, MOLECULAR MODELING AND BIOLOGICAL ACTIVITY AGAINST ARTEMIA SALINA OF NEW SYMMETRICAL BISPHOSPHORAMIDATES

A series of N,N′-bis(dialkylphosphoryl)diamines were prepared by Todd-Atherton reaction of dialkylphosphites with symmetrical diamines in a biphasic system. They were characterized by IR, 1 H-NMR, 13C-NMR and mass spectroscopy. Compounds with butoxy groups, isobutoxy groups and isopropoxy groups on the phosphorus atoms showed the lowest LD50 values when tested against Artemia salina. All other compounds that showed LD50 values higher than 363 ppm are considered non toxic. The results of a molecular modeling study suggest that the biological activity of the compounds may be related to AChE inhibition. Contrary to classical organophophorus AChE inhibitors, the compounds synthestized in this study do not possess a good leaving group, which suggests that they may act only as reversible inhibitors.