Development of new 5-chromenyl-2,4-thiazolidinediones as antimicrobial agents

Authors

  • Cristina Mariana Nastasă
  • Mihaela Duma
  • Adrian Pîrnău
  • Laurian Vlase
  • Brîndușa Tiperciuc
  • Ovidiu Oniga

DOI:

https://doi.org/10.15386/cjmed-509

Keywords:

chromone, 2, 4-thiazolidinedione, antibacterial, antifungal

Abstract

Background and aims. In the context of the increasing phenomenon of microbial resistance to usual drugs, the development of new treatment strategies and new therapeutic protocols is a constant need. Thiazolidinedione and chromone represent two important scaffolds in medicinal chemistry due to their large pharmacological applicability.

Methods. We synthesized a new 5-(chromene-3-yl)methylene-2,4-thiazolidinedione starting from 6,8-dichloro-4-oxo-4H-chromene-3-carbaldehyde. Then, by treating with different α-bromoalkylarylketones, we obtained N-substituted derivatives. All new compounds were investigated for their antimicrobial potential, using the diffusion method, against Listeria monocytogenes ATCC 13932, Staphylococcus aureus ATCC 49444, Escherichia coli ATCC 25922, Salmonella typhimurium ATCC 14028 and Candida albicans ATCC 10231. Three concentrations, 10 mg/ml, 5 mg/ml and 1 mg/ml of compounds were used. The results were evaluated by the measurement of the inhibition zone diameters and compared to those of gentamicin and fluconazole respectively, as reference drugs.

Results. All new synthesized compounds were characterized using physico-chemical and spectrometric methods. They displayed modest to good antimicrobial activity. New molecules 8, 9 and 10 may represent promising candidates, showing zone inhibition diameters superior to those of reference drugs.

Conclusions. This work presents chemical synthesis, characterization and investigation of the antibacterial and antifungal potential of 5-(chromene-3-yl)methylene-2,4-thiazolidinedione derivatives, which may be worthy of future research for designing new chemical entities.

Author Biographies

Cristina Mariana Nastasă, “Iuliu Hațieganu” University of Medicine and Pharmacy, Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Cluj-Napoca, Romania

“Iuliu Hațieganu” University of Medicine and Pharmacy, Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Cluj-Napoca, Romania

Mihaela Duma, State Veterinary Laboratory for Animal Health and Food Safety, Cluj-Napoca, Romania

State Veterinary Laboratory for Animal Health and Food Safety, Cluj-Napoca, Romania

Adrian Pîrnău, National Institute for Research and Development of Isotopic and Molecular Technologies, Cluj-Napoca, Romania

NationalInstitute for Research and Development of Isotopic and Molecular Technologies, Cluj-Napoca, Romania

Laurian Vlase, “Iuliu Hațieganu” University of Medicine and Pharmacy, Faculty of Pharmacy, Department of Pharmaceutical Technology and Biopharmaceutics, Cluj-Napoca, Romania

“Iuliu Hațieganu” University of Medicine and Pharmacy, Faculty of Pharmacy, Department of Pharmaceutical Technology and Biopharmaceutics, Cluj-Napoca, Romania

Brîndușa Tiperciuc, “Iuliu Hațieganu” University of Medicine and Pharmacy, Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Cluj-Napoca, Romania

“Iuliu Hațieganu” University of Medicine and Pharmacy, Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Cluj-Napoca, Romania

Ovidiu Oniga, “Iuliu Hațieganu” University of Medicine and Pharmacy, Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Cluj-Napoca, Romania

“Iuliu Hațieganu” University of Medicine and Pharmacy, Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Cluj-Napoca, Romania

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Published

2015-09-20

How to Cite

1.
Nastasă CM, Duma M, Pîrnău A, Vlase L, Tiperciuc B, Oniga O. Development of new 5-chromenyl-2,4-thiazolidinediones as antimicrobial agents. Med Pharm Rep [Internet]. 2015 Sep. 20 [cited 2025 Oct. 5];89(1):122-7. Available from: https://medpharmareports.com/index.php/mpr/article/view/509

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Section

Original Research