Synthesis, Characterization, and Antimicrobial Activity of Some New 2,4-Dihydro-3H-1,2,4-Triazole-3-thione Derivatives


TOK F., DAMAR ÇELİK D.

Turkish Journal of Pharmaceutical Sciences, cilt.22, sa.5, ss.349-356, 2025 (ESCI, Scopus, TRDizin) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 22 Sayı: 5
  • Basım Tarihi: 2025
  • Doi Numarası: 10.4274/tjps.galenos.2025.77834
  • Dergi Adı: Turkish Journal of Pharmaceutical Sciences
  • Derginin Tarandığı İndeksler: Emerging Sources Citation Index (ESCI), Scopus, BIOSIS, EMBASE, TR DİZİN (ULAKBİM)
  • Sayfa Sayıları: ss.349-356
  • Anahtar Kelimeler: antibacterial, antifungal, Triazole
  • Marmara Üniversitesi Adresli: Evet

Özet

Objectives: Antimicrobial resistance is a major problem in the treatment of infectious diseases. Therefore, it is important to develop new and effective antimicrobial agents. For this purpose, a new series of compounds with a 2,4-dihydro-3H-1,2,4-triazole-3-thione structure was synthesized. Materials and Methods: 2,4-dihydro-3H-1,2,4-triazole-3-thione compounds (T1-T8) were synthesized by heating thiosemicarbazide derivatives under alkaline conditions. Infrared (IR),1H-NMR, and13C-NMR spectroscopic methods were used to elucidate the chemical structures of the compounds. The antimicrobial activity of the compounds against eight bacterial strains (five Gram-negative and three Gram-positive) and two fungal strains was evaluated using the microdilution method. Results: Compounds T4, carrying a benzoyl group, and T6, carrying a phenethyl group, showed the best antibacterial activity against Enterococcus faecalis ATCC 29212, with minimum inhibitory concentrations (MICs) of 41.79 mg/L and 81.25 mg/L, respectively. Compound T6 also demonstrated the strongest antibacterial activity against Staphylococcus epidermidis ATCC 12228, with an MIC of 40.62 mg/L. Antifungal activity assays revealed that compounds T4, T6, and T8 were the most potent against Candida albicans ATCC 90028, with MIC values of 40.62–83.59 mg/L, and that T6, T7, and T8 were the most potent against Candida glabrata ATCC 90030, with MIC values of 40.62–162.5 mg/L. Conclusion: Among the compounds, T6 appears to exhibit significant antimicrobial activity against both Gram-positive bacteria (e.g., E. faecalis ATCC 29212 and S. epidermidis ATCC 12228) and fungi (e.g., Candida strains).