Synthesis and Biological Activity of Brominated Phenols with Lactamomethyl Moieties --- Natural Compounds Analogues

Abstract

This paper describes the synthesis of the brominated polyphenols with lactams fragments, which are analogues of natural marine compounds, and their biological activity research. Eight target substances were obtained with good yields via bromination of pyrrolidone and caprolactam derivatives of catechol, resorcinol, pyrogallol, phloroglucinol and propyl gallate by bromine in acetic acid or dioxane dibromide. The structures of all the obtained compounds were proved using IR spectroscopy and ¹H- and ¹³C-NMR spectrometry, and, for several compounds, by mass-spectroscopy. The composition of the target substances was confirmed using elemental analysis. For the first time it was shown that dioxane dibromide can form polybrominated aromatic derivatives, while the reaction proceeds also in ortho-position to hydroxyl groups. Results of antimicrobial activity research against various pathogenic organisms (both Gram-negative and Gram-positive, together with fungus) revealed that, among all compounds, only 1-(3,5-dibromo-2,4-dihydroxyben-zyl)pyrrolidin-2-one displayed antibacterial activity against Staphylococcus epidermidis INA 01254 with minimum inhibitory concentration equals to 16 µg/ml

Please cite this article as:

Vorobyev S.V., Starostin A.A., Vasilieva B.F., et al. Synthesis and biological activity of brominated phenols with lactamomethyl moieties --- natural compounds analogues. Herald of the Bauman Moscow State Technical University, Series Natural Sciences, 2023, no. 6 (111), pp. 134--146. DOI: https://doi.org/10.18698/1812-3368-2023-6-134-146

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