Research Article

Synthesis and Antimicrobial Evaluation of New Fluorophenyl Hybridized Thiazole and Thiadiazole Derivatives

Volume: 16 Number: 4 September 25, 2026
TR EN

Synthesis and Antimicrobial Evaluation of New Fluorophenyl Hybridized Thiazole and Thiadiazole Derivatives

Abstract

In this study, novel hybrid derivatives (4a–4e) combining 1,3-thiazole and 1,3,4-thiadiazole rings containing p-fluorophenyl on the same molecule were synthesized and their structures were elucidated using 1H-NMR and 1³C-NMR spectroscopic methods. The antimicrobial activities of the compounds were evaluated on Gram-positive bacteria (Bacillus subtilis, Staphylococcus aureus), Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa), and yeast species (Candida albicans, Candida krusei) using agar well diffusion and microdilution methods. In the diffusion test, the inhibition zone diameters ranged from 7.6 ± 0.4 to 12.3 ± 0.3 mm. The most notable activity was produced by compound 4e which produced inhibition zones of 12.3 ± 0.3 mm against E. coli, 12.0 ± 0.3 mm against P. aeruginosa and 12.0 ± 0.2 mm against C. albicans. Compound 4b was also highly effective against yeast strains, and its zone diameter against C. albicans was 12.0 ± 0.2 mm. Minimum inhibitory concentration (MIC) values were generally determined to be 1250 µg/mL for bacteria, and 625 µg/mL for some species, whereas all compounds exhibited an MIC value of 625 µg/mL against C. albicans and C. krusei. Therefore, the results obtained indicate that fluorophenyl hybrid thiazole-thiadiazole derivatives generally exhibit weak antimicrobial activity; however, it is predicted that these data will shed light on future modification studies in the context of structure-activity relationship (SAR).

Keywords

Thiazole, 1,3,4-Thiadiazole, Fluorophenyl, Antimicrobial Activity

References

  1. Abualnaja, M. M., Alalawy, A. I., Alatawi, O. M., Alessa, A. H., Qarah, A. F., Alqahtani, A. M., and El-Metwaly, N. M. (2024). Synthesis of tetrazole hybridized with thiazole, thiophene or thiadiazole derivatives and evaluation of antimicrobial activity. Saudi Pharmaceutical Journal, 32(3), 101962.
  2. Anthwal, T., Pant, S., Rana, P., and Nain, S. (2025). Design, synthesis, and in vitro, in vivo, and in silico evaluation of novel substituted 1,3,4-thiadiazole derivatives as anticonvulsant agents. Frontiers in Chemistry, 12, 1515866.
  3. Anthwal, T., Singh, H., and Nain, S. (2022). 1,3,4-Thiadiazole scaffold: Antimicrobial agents. Pharmaceutical Chemistry Journal, 55(12), 1345–1358.
  4. Boolchandani, M., D’Souza, A. W., and Dantas, G. (2019). Sequencing-based methods and resources to study antimicrobial resistance. Nature Reviews Genetics, 20(6), 356–370.
  5. Clinical and Laboratory Standards Institute. (2002). Reference method for broth dilution antifungal susceptibility testing of yeasts: Approved standard (2nd ed., M27-A2). Clinical and Laboratory Standards Institute.
  6. Clinical and Laboratory Standards Institute. (2007). Performance Standards for Antimicrobial Susceptibility Testing; Seventeenth Informational Supplement. M100-S17. CLSI 2007;27(1).
  7. Clinical and Laboratory Standards Institute. (2012). Reference methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically: Approved standard (9th ed., M07-A9). Clinical and Laboratory Standards Institute.
  8. Clinical and Laboratory Standards Institute. (2025). Performance Standards for Antimicrobial Susceptibility Testing Standards (M100-Ed35). 35th Edition, Clinical and Laboratory Standards Institute.
  9. Górecki, S., Kudelko, A., and Olesiejuk, M. (2025). Antimicrobial activity of 1,3,4-thiadiazole derivatives. Pharmaceuticals, 18(9), 1348.
  10. Gomha, S., Khalil, K., Abdel-Aziz, H., and Abdalla, M. (2015). Synthesis and antihypertensive α-blocking activity of thiazole derivatives bearing a pyrazole moiety. Heterocycles, 91(9), 1763–1773.
APA
Işık, A. (2026). Synthesis and Antimicrobial Evaluation of New Fluorophenyl Hybridized Thiazole and Thiadiazole Derivatives. Karadeniz Fen Bilimleri Dergisi, 16(4), 1486-1500. https://doi.org/10.31466/kfbd.1901669
AMA
1.Işık A. Synthesis and Antimicrobial Evaluation of New Fluorophenyl Hybridized Thiazole and Thiadiazole Derivatives. KFBD. 2026;16(4):1486-1500. doi:10.31466/kfbd.1901669
Chicago
Işık, Ayşen. 2026. “Synthesis and Antimicrobial Evaluation of New Fluorophenyl Hybridized Thiazole and Thiadiazole Derivatives”. Karadeniz Fen Bilimleri Dergisi 16 (4): 1486-1500. https://doi.org/10.31466/kfbd.1901669.
EndNote
Işık A (September 1, 2026) Synthesis and Antimicrobial Evaluation of New Fluorophenyl Hybridized Thiazole and Thiadiazole Derivatives. Karadeniz Fen Bilimleri Dergisi 16 4 1486–1500.
IEEE
[1]A. Işık, “Synthesis and Antimicrobial Evaluation of New Fluorophenyl Hybridized Thiazole and Thiadiazole Derivatives”, KFBD, vol. 16, no. 4, pp. 1486–1500, Sept. 2026, doi: 10.31466/kfbd.1901669.
ISNAD
Işık, Ayşen. “Synthesis and Antimicrobial Evaluation of New Fluorophenyl Hybridized Thiazole and Thiadiazole Derivatives”. Karadeniz Fen Bilimleri Dergisi 16/4 (September 1, 2026): 1486-1500. https://doi.org/10.31466/kfbd.1901669.
JAMA
1.Işık A. Synthesis and Antimicrobial Evaluation of New Fluorophenyl Hybridized Thiazole and Thiadiazole Derivatives. KFBD. 2026;16:1486–1500.
MLA
Işık, Ayşen. “Synthesis and Antimicrobial Evaluation of New Fluorophenyl Hybridized Thiazole and Thiadiazole Derivatives”. Karadeniz Fen Bilimleri Dergisi, vol. 16, no. 4, Sept. 2026, pp. 1486-00, doi:10.31466/kfbd.1901669.
Vancouver
1.Ayşen Işık. Synthesis and Antimicrobial Evaluation of New Fluorophenyl Hybridized Thiazole and Thiadiazole Derivatives. KFBD. 2026 Sep. 1;16(4):1486-500. doi:10.31466/kfbd.1901669