Synthesis, crystal structure, Hirshfeld surface, computational and antibacterial studies of a 9-phenanthrenecarboxaldehyde-based thiodihydropyrimidine derivative

Huseynzada A., Mori M., Meneghetti F., Israyilova A., Tuzun G., SAYIN K., ...Daha Fazla

JOURNAL OF MOLECULAR STRUCTURE, cilt.1267, 2022 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1267
  • Basım Tarihi: 2022
  • Doi Numarası: 10.1016/j.molstruc.2022.133571
  • Dergi Adı: JOURNAL OF MOLECULAR STRUCTURE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, INSPEC
  • Anahtar Kelimeler: Thiodihydropyrimidine, Hirshfeld surface analysis, Crystal structure, Molecular docking, ADME, T, POTENT, DISCOVERY, DIHYDROPYRIMIDINES, INHIBITORS, MOLECULE, PHENANTHRENE, SOLUBILITY, RESISTANCE, INSIGHTS, DESIGN
  • Sivas Cumhuriyet Üniversitesi Adresli: Evet

Özet

We report herein the synthesis of a new biologically active 3,4-dihydropyrimidin-2(1H)-thione derivative ( 4 ) from 9-phenanthrenecarboxaldehyde, thiourea, and methyl acetoacetate by the Biginelli reaction. The structure of the synthesized compound was investigated by NMR spectroscopy, mass spectrometry, and elemental analysis. Moreover, to gain insight into the conformation and crystal packing, the structure of the novel dihydropyrimidine was also studied by single-crystal X-ray diffraction. The Hirshfeld surface and contact enrichment analyses were used to better understand the molecular interactions. Considering the biological activity of dihydropyrimidines, the antibacterial effect of the synthesized compound was evaluated against A. baumanii, E. coli, P.aeruginosa, K. pneumoniae, and S. aureus; interestingly, high activ-ity was detected against S. aureus. Additionally, computational studies were performed using the Gaussian package and the Maestro Schrodinger programs, and the theoretical IR and NMR spectra of compound 4 were examined. Finally, an ADME/T analysis was performed to estimate the drug-likeness of the com-pound.(c) 2022 Elsevier B.V. All rights reserved.