Novel alpha-aminophosphonic acids. Design, characterization, and biological activity.

Novel alpha-aminophosphonic acids are synthesized reacting 1,3-oxazolidin-2-one derivatives with formaldehyde and phosphorus trichloride. Treatment of N-(phosphonomethyl)oxazolidinones with aqueous NaOH gave the expected alpha-aminophosphonic acids. The oxidation of (2-hydroxy-1,1-dimethylethylamino)methyl phosphonic acid in the presence of CdO and water resulted in N-phosphonomethyl-2-methyl-1-propanoic acid. Their structures were proved by means of IR, 1H, 13C, and 31P NMR spectroscopy. The genotoxic, clastogenic, and antiproliferative effects of newly synthesized original aminophosphonic acids were investigated for the first time.