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<p>We carried out a thiylating reaction of p-nitroacetophenone with thioglycolic acid. The reaction was carried out in a benzene solution, with a molar ratio of the initial components of 1:4. 1,1-bis-(carboxymethylthio)-1-p-nitrophenylethane (CTNE). Structural features are evaluated via Fourier transform infrared (FT-IR) spectroscopy, <sup>1</sup>H NMR and single crystal X-ray diffraction (XRD) analysis. Structure is composed of an organosulfur molecule and a water molecule. Organosulfur molecule adopted non-planar conformation supported via dihedral angle of 71.3 (4)° among carboxylic acid groups. Supramolecular organization is primarily supported via O-H⋯O bonding. Further stability of the supramolecular organization is due to π⋯π interactions with inter-centroid separation range from 3.85 to 4.01 Å. Strong and weaker interactions are evaluated via Hirshfeld surface analysis which showed that H⋯O contact has highest contribution in stability of the supramolecular organization. DFT calculations at the B3PW91/6-311 + + g (2d,2p) level was employed to optimize the molecular geometry and assess the electronic properties of the synthesized compound. Highest Occupied Molecular Orbital (HOMO)– Lowest Unoccupied Molecular Orbital (LUMO) energy gap (∆E = 4.06&#xa0;eV) of the synthesized compound indicates enhanced chemical reactivity and biological potential compared to precursor molecules. Furthermore, molecular docking studies demonstrated a promising binding affinity (-7.05&#xa0;kcal/mol) toward VEGFR2, stabilized through hydrogen bonding and hydrophobic interactions, suggesting potential anticancer activity through angiogenesis inhibition.</p> Graphical Abstract <p></p>

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Synthesis, structural features, computational study along with molecular docking examination of organosulfur mercaptoacetic acid based compound

  • 期刊论文

  • 发表日期：

    2025年11月17日

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  • Sabiya Osmanova,
  • Malahat Kurbanova,
  • Muhammad Ashfaq,
  • Mehran Feizi-Dehnayebi,
  • Muhammad Nawaz Tahir,
  • Onur Şahin

摘要

We carried out a thiylating reaction of p-nitroacetophenone with thioglycolic acid. The reaction was carried out in a benzene solution, with a molar ratio of the initial components of 1:4. 1,1-bis-(carboxymethylthio)-1-p-nitrophenylethane (CTNE). Structural features are evaluated via Fourier transform infrared (FT-IR) spectroscopy, 1H NMR and single crystal X-ray diffraction (XRD) analysis. Structure is composed of an organosulfur molecule and a water molecule. Organosulfur molecule adopted non-planar conformation supported via dihedral angle of 71.3 (4)° among carboxylic acid groups. Supramolecular organization is primarily supported via O-H⋯O bonding. Further stability of the supramolecular organization is due to π⋯π interactions with inter-centroid separation range from 3.85 to 4.01 Å. Strong and weaker interactions are evaluated via Hirshfeld surface analysis which showed that H⋯O contact has highest contribution in stability of the supramolecular organization. DFT calculations at the B3PW91/6-311 + + g (2d,2p) level was employed to optimize the molecular geometry and assess the electronic properties of the synthesized compound. Highest Occupied Molecular Orbital (HOMO)– Lowest Unoccupied Molecular Orbital (LUMO) energy gap (∆E = 4.06 eV) of the synthesized compound indicates enhanced chemical reactivity and biological potential compared to precursor molecules. Furthermore, molecular docking studies demonstrated a promising binding affinity (-7.05 kcal/mol) toward VEGFR2, stabilized through hydrogen bonding and hydrophobic interactions, suggesting potential anticancer activity through angiogenesis inhibition.

Graphical Abstract