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 activity 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 compound.

Synthesis, crystal structure, Hirshfeld surface, computational and antibacterial studies of a 9-phenanthrenecarboxaldehyde-based thiodihydropyrimidine derivative / A. Huseynzada, M. Mori, F. Meneghetti, A. Israyilova, G. Tuzun, K. Sayin, L.R. Chiarelli, C. Mutlu, M. Demiralp, U. Hasanova, V. Abbasov. - In: JOURNAL OF MOLECULAR STRUCTURE. - ISSN 0022-2860. - 1267:(2022 Nov 05), pp. 133571.1-133571.13. [10.1016/j.molstruc.2022.133571]

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

M. Mori
Secondo
;
F. Meneghetti;
2022-11-05

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 activity 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 compound.
ADME/T; Crystal structure; Hirshfeld surface analysis; Molecular docking; Thiodihydropyrimidine;
Settore CHIM/08 - Chimica Farmaceutica
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/936873
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