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.



Nitrile oxide, 1,3-dipolar cycloaddition, Ester-functionalized isoxazole, Antimicrobial activity


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.



Original Articles