Synthesis and biological evaluation of novel thioureas containing pyridine derivatives against Mycobacterium tuberculosis


YILDIRIM K., Karaçolak A. I., Kutlu E., Emen F. M., Ali M. A., ŞİMŞEK E., ...Daha Fazla

Journal of Sulfur Chemistry, 2025 (SCI-Expanded) identifier

  • Yayın Türü: Makale / Tam Makale
  • Basım Tarihi: 2025
  • Doi Numarası: 10.1080/17415993.2025.2555480
  • Dergi Adı: Journal of Sulfur Chemistry
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, Chimica
  • Anahtar Kelimeler: Anti-tuberculosis, Benzoyl thiourea, Drug-resistance tuberculosis, mycobacterium tuberculosis, Thiourea
  • Akdeniz Üniversitesi Adresli: Evet

Özet

This study aimed to synthesize and evaluate the anti-tuberculosis potential of a series of novel thiourea derivatives (1–4) containing halogenated pyridine and chlorobenzamide scaffolds. The compounds were synthesized via the reaction of appropriate pyridine derivatives with 2-chlorobenzoyl isothiocyanate and characterized by the FT-IR, 1H-NMR, 13C-NMR and ESI-MS techniques. 6–311++G (d,p) mode and B3LYP method were used in the DFT analysis to calculate the HOMO–LUMO energies of ligands 3 and 4. The calculated HOMO–LUMO transition energies indicated that 3 and 4 have low chemical hardness and may have high chemical activity. The anti-tuberculosis activity of the synthesized thioureas was investigated via the microplate nitrate reductase test method (MNRA). The 1 and 2 show less antituberculosis effect. The 3 was found to have MIC values of 16 and 32 µg/ml against the ATCC35822 (INH-R) and the ATCC35837 (EMB-R) strains, respectively. The highest value was observed with the 4 (MIC 8–128 µg/ml). The meaningful decrease in the MIC values against all the bacteria strains including the MDR isolates, which have been chosen for their clinical aspects, indicating that compound 4 may serve as a promising lead compound for the development of new anti-tuberculosis agents.