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- Title
THE STUDY OF THE INTERACTION OF 1,2- AND 1,4-NAPHTHOQUINONES WITH AMINOPHOSPHONIC ESTERS.
- Authors
Kurka, M. S.; Buchkevych, I. R.; Krvavych, A. S.; Kushil, O. V.; Karkhut, A. I.; Polovkovych, S. V.; Novikov, V. P.
- 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, IRspectroscopies 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 Â-906, Staphylococcus aureus 209-Ð, Mycobacterium luteum Â-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%.
- Subjects
NUCLEOPHILES; SULFONYL group; ESTERS; QUINONE; PHOSPHONATES; STAPHYLOCOCCUS aureus; ELEMENTAL analysis; ASPERGILLUS niger
- Publication
Issues of Chemistry & Chemical Technology / Voprosy Khimii & Khimicheskoi Tekhnologii, 2024, Issue 2, p39
- ISSN
0321-4095
- Publication type
Article
- DOI
10.32434/0321-4095-2024-153-2-39-46