Synthesis, crystal structure and in vitro anti-proliferative activity of 2-[(4-acetylphenyl)carbamoyl]phenyl acetate
Reham A. Mohamed-Ezzat,
Benson M. Kariuki,
Aladdin M. Srour
Abstract:2-[(4-Acetylphenyl)carbamoyl]phenyl acetate, C17H15NO4, has been synthesized and structurally characterized. In the structure, N—H...O hydrogen-bonding interactions form chains of molecules aligned along the [101] direction. The chains are linked by π–π and C—H...π interactions, forming a three dimensional network. The compound has been screened for in vitro anti-proliferative activity revealing considerable activity.
C17H14O6, monoclinic, P21/n (no. 14), a = 13.9003(10) Å, b = 7.6509(6) Å, c = 14.4694(11) Å, β = 105.300(3)°, V = 1484.3(2) Å3, Z = 4, R
gt(F) = 0.0357, wR
ref(F
2) = 0.0947, T = 100(2) K.
In this study, a molecular docking study was performed to propose the acetylsalicylic acid derivative 2-[(4-Acetylphenyl)carbamoyl]phenyl acetate (AMPBS) as a potential cancer candidate targeting the Epidermal Growth Factor Receptor (EGFR). The native ligand erlotinib was used as a control compound. The calculated docking score of -7.4 kcal/mol compared to the native ligand erlotinib of -7.0 kcal/mol of AMPBS compound revealed a promising anticancer activity. The stability of the complex was interpreted by careful analysis of the root mean square deviation (RMSD), root mean square fluctuations (RMSF) and mean hydrogen bond number (Hb) plots obtained from the MD trajectories. The ADMET properties of AMPBS were evaluated using relevant online tools. Drug-likeness studies showed that AMPBS is suitable for use in living organisms. It was predicted that AMPBS in the active pocket could be a promising inhibitor due to its high binding energy, interaction mechanism and retention in the active pocket.
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