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<p>A series of Dichlorobenzyloxy-chalcone derivatives containing EWG and EDG groups, along with a neutral hydrogen substituent, were synthesized and characterized by FT-IR, ¹H-NMR, ¹³C-NMR, and mass spectrometry. The antibacterial, antioxidant, and anticancer properties of the compounds were assessed in vitro, revealing notable variation in efficacy, with compound 5&#xa0;h showing promising dual anticancer activity against HCT116 and MCF-7 cell lines, 5a acting as an effective antioxidant (against DPPH), and 5i displaying the lowest MIC against <i>E. coli</i> (0.13 ± 0.00&#xa0;mg/mL), while 5e, 5f, and 5i achieved the lowest efficacy against <i>S. aureus</i> (0.17 ± 0.07&#xa0;mg/mL). In silico studies, including ADME predictions, DFT predictions, and molecular docking simulations, provided insights into the electronic properties and molecular interactions of these chalcones. Linear regression correlated quantum chemical parameters with biological activity, revealing a range of weak to strong coefficients of determination r<sup>2</sup> across the different electronic descriptors. Docking studies were conducted, and the results revealed good interactions with key protein targets. The new series uniquely incorporates a 3,4-dichlorobenzyloxy ether linkage, a structural modification designed to explore altered conformational flexibility, favorable lipophilicity, and distinct binding interactions within biological targets. Notably, the presence of dichlorobenzyl and halogen groups enhanced lipophilicity, which, in turn, improved cell membrane permeability. </p> Graphical Abstract <p></p>

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Computational and SAR Assessment of Newly Synthesized Dichlorobenzyloxy Chalcone Scaffolds with Their Biological Evaluation

  • 期刊论文

  • 发表日期：

    2026年2月11日

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  • Eman Noureddin Mohammed,
  • Media Noori Abdullah

摘要

A series of Dichlorobenzyloxy-chalcone derivatives containing EWG and EDG groups, along with a neutral hydrogen substituent, were synthesized and characterized by FT-IR, ¹H-NMR, ¹³C-NMR, and mass spectrometry. The antibacterial, antioxidant, and anticancer properties of the compounds were assessed in vitro, revealing notable variation in efficacy, with compound 5 h showing promising dual anticancer activity against HCT116 and MCF-7 cell lines, 5a acting as an effective antioxidant (against DPPH), and 5i displaying the lowest MIC against E. coli (0.13 ± 0.00 mg/mL), while 5e, 5f, and 5i achieved the lowest efficacy against S. aureus (0.17 ± 0.07 mg/mL). In silico studies, including ADME predictions, DFT predictions, and molecular docking simulations, provided insights into the electronic properties and molecular interactions of these chalcones. Linear regression correlated quantum chemical parameters with biological activity, revealing a range of weak to strong coefficients of determination r2 across the different electronic descriptors. Docking studies were conducted, and the results revealed good interactions with key protein targets. The new series uniquely incorporates a 3,4-dichlorobenzyloxy ether linkage, a structural modification designed to explore altered conformational flexibility, favorable lipophilicity, and distinct binding interactions within biological targets. Notably, the presence of dichlorobenzyl and halogen groups enhanced lipophilicity, which, in turn, improved cell membrane permeability.

Graphical Abstract