Structural and biological aspects of ( tert -butoxycarbonylamino)propylphosphonate derivatives

A promising trend in the search for new more effective and selective drugs is the search for structural analogues of amino acids. The structures and activities of both enantiomeric diethyl (1S,2R)- and (1R,2S)-1,2-bis(tert-butoxycarbonylamino)propylphosphonates (as the monohydrates, C₁₇H₃₅N₂O₇P·H₂O), 1 and 2, respectively, and racemic diethyl (RS)-2-(tert-butoxycarbonylamino)propylphosphonate, 3, have been determined. The antimicrobial activity of 1, 2 and 3 was tested against reference bacterial strains and showed weak bioactivity against Gram-positive bacteria. ADME (absorption, distribution, metabolism and excretion) analysis indicates that the compounds may have gastrointestinal absorption. The compounds satisfy Lipinski's rules.