Synthesis, spectroscopic and electronic structure analyses, DFT studies and molecular docking applications of isatin hydrazone derivatives

ERKAN S., Yıldız C. A.

Journal of Molecular Structure, cilt.1327, 2025 (SCI-Expanded) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1327
  • Basım Tarihi: 2025
  • Doi Numarası: 10.1016/j.molstruc.2024.141150
  • 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: Computational chemistry, Isatin bis-hydrazone, Molecular Docking, Synthesis
  • Sivas Cumhuriyet Üniversitesi Adresli: Evet

Özet

The derivatives of isatin bis-hydrazone compounds formed by adding electron-withdrawing and electron-donating substituents (S1-S7) were synthesized. Chemical structure characterizations of the synthesized compounds were elucidated by spectroscopic (IR, 1H-NMR, 13C-NMR, LC-QTOF-MS) methods. S1-S7 compounds were optimized with B3LYP/6–31G(d,p) level. 1H-NMR and 13C-NMR spectra and chemical shifts were calculated for the compounds at the GIAO/B3LYP/6–31G(d,p) level. Experimental and calculated IR, 1H-NMR, and 13C-NMR data were compared with each other. Electronic differences created by substituent effects in the skeletal structure were investigated with frontier molecular orbitals contour diagrams and Molecular Electrostatic (MEP) maps. Activities of the designed chemicals against biological receptors at the molecular scale were calculated with docking studies. Compounds S1-S7 were docked to target proteins with PDB ID: 1JNX and 2HQ6 representing breast and colon cancer cells, respectively. Chemical structures with high activity potential were synthesized in the light of the information obtained from the docking results.