Novel 2-methoxy-4-(((3-methyl-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl)-imino)-methyl)-phenyl benzoate as a potential drug candidate: Synthesis, spectroscopy, TD-DFT, NBO, TDM, FMO, MEP, molecular docking, and molecular dynamics studies

Harmankaya A., Medetalibeyoğlu H., Buğra Ortaakarsu A., Atalay A., Manap S., Koca E., ...Daha Fazla

Journal of Molecular Structure, cilt.1338, 2025 (SCI-Expanded, Scopus) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1338
  • Basım Tarihi: 2025
  • Doi Numarası: 10.1016/j.molstruc.2025.142286
  • Dergi Adı: Journal of Molecular Structure
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, Chimica, Compendex, INSPEC
  • Anahtar Kelimeler: Molecular docking, Molecular dynamic simulations, NBO, TDM, Triazole
  • Gazi Üniversitesi Adresli: Evet

Özet

A promising novel drug candidate, 2‑methoxy-4-[((3-methyl-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl)-imino)-methyl]-phenyl benzoate (3), has been successfully synthesized through the condensation reaction of 4-formyl-2-methoxyphenyl benzoate and 4-amino-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one. The synthesis process demonstrated a good yield, and the compound underwent thorough characterization using 1H\13C NMR, IR, and UV–Vis spectroscopic techniques. A newly synthesized compound, 2‑methoxy-4-(((3-methyl-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl)-imino)-methyl)-phenyl benzoate (3), has been performed structural analysis utilizing a combination of experimental and theoretical methods. The analysis process involved the use of FT-IR and NMR spectroscopy alongside the evaluation of various electronic parameters, including global reactivity parameters, FMO, NBO, MEP, ELF, LOL, TDM, NLO, and UV, using the IEFPCM model. A comprehensive molecular docking study was conducted to analyze the binding mode interactions between compound 3 and the targeted enzymes (AChE, BChE, COX-1, and COX-2). The results indicate that the strength of intermolecular hydrogen bonding in ligand-receptor complexes is crucial in explaining the observed inhibition outcomes. Furthermore, molecular dynamics simulations are conducted to analyze the protein-ligand complex and assess the stability of the compound within a protein environment.