Aminophosphonate Explained

Aminophosphonates are organophosphorus compounds with the formula (RO)₂P(O)CR'₂NR"₂. These compounds are structural analogues of amino acids in which a carboxylic moiety is replaced by phosphonic acid or related groups.^[1] Acting as antagonists of amino acids, they inhibit enzymes involved in amino acid metabolism and thus affect the physiological activity of the cell. These effects may be exerted as antibacterial, plant growth regulatory or neuromodulatory. They can act as ligands, and heavy metal complexes with aminophosphonates have had medical applications investigated.^[2]

Phosphonates are more difficult to hydrolyse than phosphates.^[3]

Preparation

Aminophosphonates are often prepared by hydrophosphonylation, usually the condensation of imines and phosphorous acid. In the Pudovik reaction or Kabachnik–Fields reaction the esters of phosphorous acid are employed, e.g. diphenylphosphite. Because these compounds are of pharmaceutical interest, methods have been developed to induce these additions asymmetrically.^{[4] [5]}

Notes and References

1. 350. 9. 2008. 1195–1208. Catalytic Enantioselective Hydrophosphonylation of Aldehydes and Imines. Pedro Merino. Eugenia Marqués-López. Raquel P. Herrera. Advanced Synthesis & Catalysis. 10.1002/adsc.200800131. 10261/114023. free.
2. Tušek-Božić. LJ. Aminophosphonate metal complexes of biomedical potential. Current Medicinal Chemistry. 2013. 20. 16. 2096–117. 23432587. 10.2174/0929867311320160004.
3. Orsini. F. Sello. G. Sisti. M. Aminophosphonic acids and derivatives. Synthesis and biological applications.. Current Medicinal Chemistry. 2010. 17. 3. 264–89. 20214568. 10.2174/092986710790149729.
4. 6. 9. 2016. 5915–5924. Synthesis of new α-aminophosphonate derivatives incorporating benzimidazole, theophylline and adenine nucleobases using L-cysteine functionalized magnetic nanoparticles (LCMNP) as magnetic reusable catalyst: evaluation of their anticancer properties. Foroogh Bahrami. Farhad Panahi. Ali Khalafinezhad. RSC Advances. 10.1039/C5RA21419J . 2016RSCAd...6.5915B. 10261/114023.
5. 10.1021/jm200587f. Remarkable Potential of the α-Aminophosphonate/Phosphinate Structural Motif in Medicinal Chemistry. 2011. Mucha. Artur. Kafarski. Paweł. Berlicki. Łukasz. Journal of Medicinal Chemistry. 54. 17. 5955–5980. 21780776.