Synthesis, characterization and computational studies on (E)-4-(1-((2-hydroxyphenyl)imi no) hexyl)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one

Ukwueze N. N., Ezeorah C. J., Onyeyilim E. L., Uzoewulu C. P., Okoro U. C., Ukoha P. O., ...Daha Fazla

JOURNAL OF MOLECULAR STRUCTURE, cilt.1323, 2025 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1323
  • Basım Tarihi: 2025
  • Doi Numarası: 10.1016/j.molstruc.2024.140552
  • 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
  • Ondokuz Mayıs Üniversitesi Adresli: Evet

Özet

A coupling precursor, 4-hexanoyl-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, 1 synthesized by the reaction of 3-methyl-1-phenyl-1H-pyrazol-5-one with hexanoyl chloride was reacted with 2-aminophenol to synthesize (E)-4-(1-((2-hydroxyphenyl)imino)hexyl)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, 1a. The compounds were characterized by conventional spectroscopic techniques, 1H and 13C NMR, UV-Visible, FTIR spectroscopy and single crystal X-ray crystallograpic structural determinations and computational techniques. To augment the experimental data, DFT calculations were carried. Molecular dockings were used to predict the interactions between, 1a with some biological targets. The binding free energies in the Plasmepsin II active sites indicated anti-malarial activity against P. falciparum in epidermal growth factor receptor (EGFR) inhibition, anti-inflammatory properties against human peroxiredoxin 5, and anticancer properties. With binding energies less than -5.00 kcal/mol, the results indicate that 1a is a potential drug target for anti-inflammatory, antimalarial and anti-cancer properties.