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., ...More

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

  • Publication Type: Article / Article
  • Volume: 1267
  • Publication Date: 2022
  • Doi Number: 10.1016/j.molstruc.2022.133571
  • Journal Name: JOURNAL OF MOLECULAR STRUCTURE
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, INSPEC
  • Keywords: Thiodihydropyrimidine, Hirshfeld surface analysis, Crystal structure, Molecular docking, ADME, T, POTENT, DISCOVERY, DIHYDROPYRIMIDINES, INHIBITORS, MOLECULE, PHENANTHRENE, SOLUBILITY, RESISTANCE, INSIGHTS, DESIGN
  • Sivas Cumhuriyet University Affiliated: Yes

Abstract

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.