2025, Vol. 6, Issue 2, Part C
Synthesis, characterization, and theoretical (DFT) analysis of new schiff bases derived from 4-aminoantipyrin for molecular docking and biological activity
Author(s): Mohammad M Al-Tufah, Anaam Khalif Al-Azzawy and Diaa M Najim
Abstract: Schiff bases have important applications in biological activities and combating harmful bacteria, so they are important in the medical and pharmaceutical aspects. They can be synthesized from the reaction of compounds containing carbonyl groups (aldehydes and ketones) with compounds containing a free amine group (primary amines). In this research, new Schiff base derivatives were prepared through addition and condensation reactions by adding 4-aminoantipyrene to substituted aromatic aldehydes (2,4-dichlorobenzaldehyde and 4-methoxybenzaldehyde) and substituted aromatic ketones (acetophenone and 2-hydroxyacetophenone) in addition to sulfanilic acid. The catalyst was glacial acetic acid, and ethanol was used as a solvent. The prepared compounds were characterized by FT-IR spectroscopy. 1H-NMR and 13C-NMR were used to characterize the structures of some of them. In addition, mass spectrometry was used to verify the successful preparation of compounds A1 and A2. The biological activity of the prepared compounds A1, A4, and A5 was studied against two types of bacteria: Gram-negative (Klebsiella) and Gram-positive (Staphylococcus aureus and Enterococcus faecalis). The compounds showed broad activity at high concentrations (0.01, 0.001 mg/ml), while the activity of these compounds decreased at high concentrations. To understand the biological activity of compounds A1 and A4, molecular docking was studied, and the results showed that the binding strength of these compounds to the active site of the protein is (-7.86, -7.63 Kcal/mol) compared to the standard compound (-8.62 Kcal/mol). To determine the electronic properties of the prepared compounds, the density-to-energy-band theory (DFT) was used, and it was found that compound A1 has the smallest energy gap among the compounds. The distribution of partial charges of the prepared compounds was also measured.
DOI: 10.22271/reschem.2025.v6.i2c.224
Pages: 182-200 | Views: 125 | Downloads: 51
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How to cite this article:
Mohammad M Al-Tufah, Anaam Khalif Al-Azzawy, Diaa M Najim. Synthesis, characterization, and theoretical (DFT) analysis of new schiff bases derived from 4-aminoantipyrin for molecular docking and biological activity. J Res Chem 2025;6(2):182-200. DOI: 10.22271/reschem.2025.v6.i2c.224
