Abstract
The synthesis of new substituted arylphosphoramidates is performed in two steps through phosphorylation of the corresponding alcohols followed by aminolysis. The formation of the desired phosphoramidates depends on the subsequent addition of the two alcohols with the amine being added at the last step. The products were obtained in 58–95% yields. They were characterized mainly by multinuclear (1H, 13C, 31P, and 19F) NMR and IR spectroscopy. In addition, the antimicrobial and antiacetylcholinesterase activities were evaluated. The results showed acetylcholinesterase activity by some compounds, whilst no significant inhibitory effect against the tested bacterial strains has been recorded.
Highlights
Organophosphorus compounds are widely used as pesticides and chemical weapon agents because of their inhibitory effect on acetylcholinesterase [1]
Recent studies have shown that phosphoramidates and phosphates can be used as anticancer agents [4, 5], anti-HIV [6], and against Alzheimer’s disease [7]. It was shown [8] that some phosphoramidates are active against strains of Bacillus subtilis, Escherichia coli, Staphylococcus aureus, and Streptococcus mutans. It was shown [9] that they are bacterial enzyme inhibitors, aspartate semialdehyde dehydrogenase (ASA-DH), which is involved in the biosynthesis of the aspartate family of amino acids
All synthesized phosphoramidates were characterized by 31P NMR, 1H, and 13C NMR, IR spectroscopy
Summary
Organophosphorus compounds are widely used as pesticides and chemical weapon agents because of their inhibitory effect on acetylcholinesterase [1]. Recent studies have shown that phosphoramidates and phosphates can be used as anticancer agents [4, 5], anti-HIV [6], and against Alzheimer’s disease [7]. It was shown [8] that some phosphoramidates are active against strains of Bacillus subtilis, Escherichia coli, Staphylococcus aureus, and Streptococcus mutans. It was shown [9] that they are bacterial enzyme inhibitors, aspartate semialdehyde dehydrogenase (ASA-DH), which is involved in the biosynthesis of the aspartate family of amino acids. P-nitrophenylphosphoramidate derivatives were proven to be considerably stronger [11]
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