The study of the interaction of 1,2- and 1,4-naphthoquinones with aminophosphonic esters

Abstract

A number of new biologically active phosphorus-containing quinones were prepared by the reaction of 2,3-dichloro-1,4-naphthoquinone and sodium 1,2-naphthoquinone-4-sulfonate with phosphonate nucleophilic reagents, aminophosphonic acid esters. The structures of the synthesized compoumds were confirmed by ESI-MS, 1H NMR, IR-spectroscopies and elemental analysis. It was shown that aminophosphonic esters form products of nucleophilic substitution of a chlorine atom of 1,4-naphthoquinone or a sulfonyl group of 1,2-naphthoquinone on an aminophosphonic fragment. The products of the interaction of sodium 1,2-naphthoquinone-4-sulfonate with primary aminophosphonates existed in solution in 1,2-quinoid or 2-hydroxy-1,4-quinonimine tautomeric form depending on pH. The antimicrobial activity of the prepared compounds was investigated against Escherichia coli В-906, Staphylococcus aureus 209-Р, Mycobacterium luteum В-917, Candida tenuis VKM Y-70 and Aspergillus niger VKM F-1119 strains by the method of diffusion in agar of their 0.1% and 0.5% solutions. 1,2-Naphthoquinone derivatives showed good activity against S. aureus at a concentration of 0.1%, in its turn 1,4-napthoquinone derivatives showed activity against M. luteum at a concentration of 0.5%.