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Potent Antimicrobial Azoles: Synthesis, In Vitro and In Silico Study.

Zeynep Özdemir1, Yaren Nur Zenni1, Arzu Karakurt2

  • 1Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Inonu University, 44280 Malatya, Türkiye.

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|November 27, 2024
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Summary

New azole derivatives with oxime ether functionality show potent broad-spectrum antifungal and antibacterial activities. Compounds 5c and 5h demonstrated superior efficacy against dermatophytes and bacteria, suggesting potential in antimicrobial chemotherapy.

Keywords:
(arylalkyl)azoleantifungal activitydermatophytesimidazolemolecular modellingoxime ether

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Area of Science:

  • Medicinal Chemistry
  • Antimicrobial Drug Discovery
  • Organic Synthesis

Background:

  • Invasive fungal infections pose significant mortality risks, especially in immunocompromised individuals.
  • Azole antifungals are widely used due to their efficacy and safety.
  • Oxime ether functionality in antifungals presents novel antimicrobial potential.

Purpose of the Study:

  • To synthesize and evaluate novel oxime ether derivatives of azole scaffolds for antimicrobial activity.
  • To identify compounds with broad-spectrum antifungal and antibacterial properties.

Main Methods:

  • Synthesis of eleven new oxime ether azole derivatives (compounds 5a-k).
  • Antimicrobial susceptibility testing using the microdilution method.
  • Molecular docking studies against fungal CYP51 and bacterial FtsZ proteins.

Main Results:

  • Compounds 5c and 5h exhibited potent antifungal activity against dermatophytes, outperforming griseofulvin.
  • Compounds 5c and 5h showed significant antibacterial activity against Gram-positive and Gram-negative bacteria, surpassing ciprofloxacin.
  • Molecular docking indicated favorable interactions with fungal lanosterol 14α-demethylase (CYP51) and bacterial FtsZ.

Conclusions:

  • The synthesized oxime ether azole derivatives possess broad-spectrum antifungal and antibacterial effects.
  • Compounds 5c and 5h are promising candidates for further development in antimicrobial chemotherapy.
  • The oxime ether moiety is a valuable addition to the azole scaffold for enhanced antimicrobial activity.