SYNTHESIS, CHARACTERIZATION AND BIO-ACTIVITY OF SOME NEW α-AMINOPHOSPHONATES

Abstract

A convenient and efficient one-pot reaction has been employed for the synthesis of new α-aminophosphonates 4a-4k via Kabachnik-Fields reaction in 65-82 % yields. In the procedure developed, equimolar quantities of 2-amino-4-methylphenol 1, various aromatic aldehydes 2a-2k and dimethylphosphite 3 in dry toluene were reacted under reflux for 4-6 h. The products were characterized by IR, ¹H, ¹³C and ³¹P NMR spectra and elemental analysis. All the synthesized compounds were screened for in vitro antibacterial activity ( Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Klebsiella pneumoniae, Salmonella typhimurium) and antifungal activity ( Candida albicans, Aspergillus niger). 4a showed potent activity with lowest MIC value.
KEY WORDS: α-Aminophosphonate, Kabachnik-fields reaction, Antibacterial and antifungal activities


Bull. Chem. Soc. Ethiop. 2009, 23(1), 69-75.