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Synthesis and Antimicrobial Activity of 3-Substituted 8-Propenylbenzo[e][1,3]oxazines

  • Organic Synthesis and Industrial Organic Chemistry
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Abstract

A series of 1,3-benzoxazine derivatives were prepared by ternary Mannich condensation of 2-propenylphenol, formaldehyde, and primary amines (aniline, propylamine, hexylamine, and benzylamine). The product structures were confirmed by elemental analysis and by IR and NMR spectroscopy. The antimicrobial activity of the compounds against Staphylococcus aureus (two strains), Escherichia coli, Candida albicans, Shigella flexneri, Salmonella enterica, and Aspergillus niger was evaluated in 5, 15, and 35 mg L–1 solutions. The benzoxazine containing the benzyl fragment shows the best antimicrobial properties. To confirm the antimicrobial activity of the compounds in lower concentrations, serial dilution tests were performed, and the minimal suppressing concentration (0.035 mg L–1) was determined. The ultrastructure of an Escherichia coli cell in the presence of the compound with the benzyl substituent was examined by electron microscopy.

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ACKNOWLEDGMENTS

The author is sincerely grateful to the head of the Microbiological Department, Republican Sanitary and Quarantine Inspection, Ministry of Health, PhD (Biol.) G.A. Guliyeva for the assistance in studying the antimicrobial properties of the synthesized compounds and to senior researcher of the Laboratory of Electron Microscopy, Azerbaijan Medical University, PhD (Med.) F.G. Rzayev for the assistance in studying the ultrastructure of an E. сoli cell by electron microscopy.

Funding

The study was financially supported by the Foundation for Science Development at the President of the Azerbaijan Republic, grant no. EIF/MQM/Elm-Tehsil-1-2016-1(26)-71/01/3.

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Correspondence to G. M. Mehdiyeva.

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Translated from Zhurnal Prikladnoi Khimii, No. 2, pp. 253–259, February, 2022 https://doi.org/10.31857/S0044461822020063

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Mehdiyeva, G.M. Synthesis and Antimicrobial Activity of 3-Substituted 8-Propenylbenzo[e][1,3]oxazines. Russ J Appl Chem 95, 277–283 (2022). https://doi.org/10.1134/S1070427222020070

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