Synthesis, characterization and in silico study of (E)-4‑bromo-2-(1-(2-phenylhydrazineylidene)ethyl)phenol for antioxidant activity and for the inhibition of enzymes
Abstract
A new hydrazone–Schiff base was synthesised through the reaction of phenylhydrazine with an acetophenone derivative in a methanolic medium. The target compound was successfully obtained as brown crystals in a high yield. Its structure was thoroughly characterised using various spectroscopic techniques, including FTIR, UV–Vis, LC–MS, 1 H NMR, 13 C NMR, and DEPT-135. Furthermore, the structure of ( E )-4-bromo-2-(1-(2-phenylhydrazinylidene)ethyl)phenol (HSBr) was confirmed by two-dimensional (2D) NMR (HSQC and HMBC), which showed the correlation between the carbon and hydrogen atoms within the molecule. The antioxidant activities of HSBr were evaluated in vitro using ABTS •+ scavenging, FRAP, and phenanthroline assay. The results demonstrated that HSBr exhibited notable antioxidant activity, with an IC 50 value of 11.69 ± 0.01 μM, A 0.5 = 20.87 ± 0.03 μM, and A 0.5 = 6.35 ± 0.02 μM in the ABTS, FRAP, and phenanthroline assay respectively. Additionally, the compound showed promising enzyme inhibitory activity against acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and urease, with IC₅₀ values of 41.04 ± 0.09 μM, 117.93 ± 0.14 μM, and 56.16 ± 0.28 μM, respectively. Moreover, in silico molecular docking simulations were conducted to examine the antioxidant potential, the anticholinesterase and urease inhibitory activity of HSBr with the proteins 2E1Q, 2CDU, 1OG5, 2×08, 3MNG 4EY7, 4BDS, and 3LA4. Molecular properties of HSBr were investigated using density functional theory (DFT) at the B3LYP/6-311+G(d,p) level. The electronic properties, molecular electrostatic potential (MESP), Mulliken atomic charges, and chemical reactivity and stability were calculated to determine potential regions for electrophilic and nucleophilic attack in the molecule. In summary, the computational results were in good agreement with the experimental findings, thereby confirming the proposed molecular structure and properties.
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BibTeX
@article{chaabane2026synthesis,
title = {{Synthesis, characterization and in silico study of (E)-4‑bromo-2-(1-(2-phenylhydrazineylidene)ethyl)phenol for antioxidant activity and for the inhibition of enzymes}},
author = {Widad Chaabane and Salim Madani and Kamel Mokhnache and Rania Chaima Bouabdallah and Chawki Bensouici and Redouane Tabti and Moussa Boudiaf and Lokmane Abdelouahed},
journal = {Journal of Molecular Structure},
year = {2026},
month = sep,
doi = {10.1016/j.molstruc.2026.147470},
url = {https://hal.science/hal-05772344v1},
note = {CC BY},
}
RIS
TY - JOUR
TI - Synthesis, characterization and in silico study of (E)-4‑bromo-2-(1-(2-phenylhydrazineylidene)ethyl)phenol for antioxidant activity and for the inhibition of enzymes
AU - Widad Chaabane
AU - Salim Madani
AU - Kamel Mokhnache
AU - Rania Chaima Bouabdallah
AU - Chawki Bensouici
AU - Redouane Tabti
AU - Moussa Boudiaf
AU - Lokmane Abdelouahed
PY - 2026
DA - 2026/09/30
JO - Journal of Molecular Structure
DO - 10.1016/j.molstruc.2026.147470
UR - https://hal.science/hal-05772344v1
AB - A new hydrazone–Schiff base was synthesised through the reaction of phenylhydrazine with an acetophenone derivative in a methanolic medium. The target compound was successfully obtained as brown crystals in a high yield. Its structure was thoroughly characterised using various spectroscopic techniques, including FTIR, UV–Vis, LC–MS, 1 H NMR, 13 C NMR, and DEPT-135. Furthermore, the structure of ( E )-4-bromo-2-(1-(2-phenylhydrazinylidene)ethyl)phenol (HSBr) was confirmed by two-dimensional (2D) NMR (HSQC and HMBC), which showed the correlation between the carbon and hydrogen atoms within the molecule. The antioxidant activities of HSBr were evaluated in vitro using ABTS •+ scavenging, FRAP, and phenanthroline assay. The results demonstrated that HSBr exhibited notable antioxidant activity, with an IC 50 value of 11.69 ± 0.01 μM, A 0.5 = 20.87 ± 0.03 μM, and A 0.5 = 6.35 ± 0.02 μM in the ABTS, FRAP, and phenanthroline assay respectively. Additionally, the compound showed promising enzyme inhibitory activity against acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and urease, with IC₅₀ values of 41.04 ± 0.09 μM, 117.93 ± 0.14 μM, and 56.16 ± 0.28 μM, respectively. Moreover, in silico molecular docking simulations were conducted to examine the antioxidant potential, the anticholinesterase and urease inhibitory activity of HSBr with the proteins 2E1Q, 2CDU, 1OG5, 2×08, 3MNG 4EY7, 4BDS, and 3LA4. Molecular properties of HSBr were investigated using density functional theory (DFT) at the B3LYP/6-311+G(d,p) level. The electronic properties, molecular electrostatic potential (MESP), Mulliken atomic charges, and chemical reactivity and stability were calculated to determine potential regions for electrophilic and nucleophilic attack in the molecule. In summary, the computational results were in good agreement with the experimental findings, thereby confirming the proposed molecular structure and properties.
SN - 0022-2860
SN - 0022-2860
ER -