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Synthesis and antimicrobial activity of some ester functionalized isoxazoles incorporating anthracene moieties via nucleophilic substitution reaction

Sarbast M. Ahmed
Department of Pharmaceutical Chemistry, College of Pharmacy, Hawler Medical University, Erbil, Iraq.
Hewa Omer Ahmed
Department of Pharmaceutical Chemistry, College of Pharmacy, Hawler Medical University, Erbil, Iraq.
Faiq H. S. Hussain
Department of Medical Analysis, Faculty of Applied Science, Tishk International University, Erbil, Iraq.
Hayman Sardar Abdulrahman
Department of Pharmaceutical Chemistry, College of Pharmacy, Hawler Medical University, Erbil, Iraq.
Hemn A. Qader
Department of Pharmaceutical Chemistry, College of Pharmacy, Hawler Medical University, Erbil, Iraq.
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Copyright (c) 2023 sarbast M. Ahmed, Hewa Omer Ahmed, Faiq H. S. Hussain, Hayman Sardar Abdulrahman, Hemn A. Qader (Author)

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Abstract

Background and objective: Five-membered heterocycle compounds having single oxygen and nitrogen atom at adjacent positions are known as isoxazoles. Isoxazole compounds have a broad range of biological activities and therapeutic value. In view of a strategic design of antimicrobial compounds, several new ester-functionalized isoxazoles were synthesized and characterized.

Methods: A regioselective isoxazole incorporating an anthracene moiety was adducted via an effective 1,3-dipolar cycloaddition between anthracene nitrile oxide and propargyl bromide as a dipolarophile.

Results: Synthesized isoxazole 4 underwent nucleophilic substitution reaction to produce unprecedented ester-functionalized isoxazoles 6a-j, by condensation with equimolar amounts of different generated in situ sodium carboxylate upon dissolving in acetonitrile with refluxing. The chemical structure of all target compounds was proved by (FT-IR, 1H-NMR, and APT13C-NMR) techniques and their antibacterial and antifungal activities was evaluated.

Conclusion: Allnewly synthesizedcompounds6 a-j have been obtained in good yields after purification by column chromatography. They showed significant antibacterial and antifungal activity after screening against two bacterial strains, Escherichia coli and Staphylococcus aureus and a fungi strain, Candida albicans, using disc diffusion method.

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How to Cite
M. Ahmed, S., Omer Ahmed, H., H. S. Hussain, F. ., Sardar Abdulrahman, H., & A. Qader, H. (2023). Synthesis and antimicrobial activity of some ester functionalized isoxazoles incorporating anthracene moieties via nucleophilic substitution reaction. Zanco Journal of Medical Sciences (Zanco J Med Sci), 27(2), 213–226. https://doi.org/10.15218/zjms.2023.024

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