Design and one-pot synthesis of new α-aminophosphonates and antimicrobial activity

Abstract

Background: α-Aminophosphonates are bioisosters of amino acids and have several
pharmacological effects. α-Aminophosphonates have been synthesized by various
routes from reaction between an amine, an aldehyde, and phosphate compounds.
Materials and Methods: We synthesized 20 new α-aminophosphonates in the presence
of FeCl3 in THF as a catalyst to facilitate the Manich-type reaction of aldehyde, amine and
phosphite compounds to form the corresponding α-aminophosphonates in a one-pot,
three-component reaction. In this study, the catalytic effect of ZnCl2 was also compared
with FeCl3 in the synthesis of α-aminophosphonates. Results: The results showed that
FeCl3 catalyzed the reaction in mild conditions to form α-aminophosphonates with high
yields, but ZnCl2 did not give high yields of the compounds and the reaction took longer
time in comparison to that taken by FeCl3 The chemical structures of all new compounds
were confirmed by spectrophotometric methods (1HNMR, 13CNMR, IR). The
compounds were investigated for antimicrobial activity against Escherichia coli, Bacillus
subtilis, Salmonella typhi, Shigella sonnei, Proteus vulgaris, and Staphylococcus epidermidis.
Conclusion: The new synthesized compounds did not show good antibacterial activity
against the tested microorganisms