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Journal of Pharmaceutical Negative Results
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Year : 2011  |  Volume : 2  |  Issue : 2  |  Page : 78-86

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

Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Shiraz University of Medical Sciences, Shiraz, Iran

Correspondence Address:
Soghra Khabnadideh
Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Shiraz University of Medical Science, Shiraz
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Source of Support: Financial assistance from the Shiraz University of Medical Sciences, Conflict of Interest: None

DOI: 10.4103/0976-9234.90219

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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

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