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

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 antimicrobi...

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Bibliographic Details
Published in:Russian journal of applied chemistry 2022, Vol.95 (2), p.277-283
Main Author: Mehdiyeva, G. M.
Format: Article
Language:English
Subjects:
Amines
Aniline
Antiinfectives and antibacterials
Benzoxazines
Chemical analysis
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Condensates
Dilution
E coli
Industrial Chemistry/Chemical Engineering
Infrared spectroscopy
NMR spectroscopy
Organic Synthesis and Industrial Organic Chemistry
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Summary: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.
ISSN:1070-4272
1608-3296
DOI:10.1134/S1070427222020070