Mono- and bis-1,4-naphthoquinone thioethers: synthesis, electrochemical properties, antioxidant and antibacterial activity.

Autor: Galustyan, A., Burmistrova, D. A., Fokin, V. A., Simeonova, K. S., Polovinkina, M. A., Pomortseva, N. P., Baranov, E. V., Almyasheva, N. R., Smolyaninov, I. V., Poddel'sky, A. I., Berberova, N. T.
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Zdroj: Russian Chemical Bulletin; Mar2024, Vol. 73 Issue 3, p714-727, 14p
Abstrakt: New sulfur-containing mono- and bis-1,4-naphthoquinone thioethers, which are thiolated analogs of vitamin K, were synthesized. The molecular structure in the crystal-line state of the thioether with a pyrazinylethyl substituent at the sulfur atom was determined by X-ray diffraction analysis. The electrochemical transformations and spectral properties in the UV-vis range of the spectrum were studied for the obtained compounds. Most bis-1,4-naphthoquinone thioethers are characterized by two reversible two-electron reduction processes. The compound with a diphenyl sulfide bridging linker was found to have four cathodic stages corresponding to the sequential reduction of naphthoquinone fragments. Sulfides containing two naphthoquinone fragments showed the highest radical scavenging activity. The studied compounds exerted an anti/prooxidant effect in the process of lipid peroxidation of rat liver homogenate in vitro depending on the time of incubation. The thioethers exhibited antibacterial activity (9.76–78.13 µg mL−1) against Gram-positive bacteria (S. aureus ATCC 6538 and ATCC 43300, E. faecium ATCC 3576 and ATCC 28212). [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index