Crystal Structure, Hirshfeld Surface Analysis and Comparative Docking Study of 2-Amino-5-Oxo-4-Phenyl-5,6,7,8-Tetrahydro-4<i>H</i>-Chromene-3-Carbonitrile-1,4-Dioxane

Karadağ Alpaslan M., Alpaslan M. K., Poyraz E. B., Albayati M. R., Salim Jasim S., Dege N.

JOURNAL OF STRUCTURAL CHEMISTRY, cilt.66, sa.6, ss.1147-1161, 2025 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 66 Sayı: 6
  • Basım Tarihi: 2025
  • Doi Numarası: 10.1134/s0022476625060034
  • Dergi Adı: JOURNAL OF STRUCTURAL CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, INSPEC
  • Sayfa Sayıları: ss.1147-1161
  • Ondokuz Mayıs Üniversitesi Adresli: Evet

Özet

This study explores the synthesis, crystal structure, Hirshfeld surface analysis, and molecular docking of 2-amino-5-oxo-4-phenyl-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile-1,4-dioxane, a biologically relevant chromene derivative. The compound was synthesized via a one-pot multicomponent reaction, and X-ray diffraction confirmed its structure. Hirshfeld analysis showed dominant H & ctdot;H, C & ctdot;H, and O & ctdot;H interactions, indicating significant hydrogen bonding and Van der Waals forces. Molecular docking against CYP1A2, a key enzyme in drug metabolism, revealed a binding energy of -6.56 kcal/mol, surpassing reference drugs like anagrelide, caffeine, and ofloxacin. Strong hydrogen bonds and hydrophobic interactions suggest its potential as a CYP1A2 inhibitor, important for drug interactions and metabolism. These findings support its drug development potential, either as a therapeutic agent or a lead compound for designing more effective inhibitors.