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<p>We synthesized a series of dibutyl (2,2-dicyano-1-phenylethyl) phosphonates using a solvent-free, one-pot reaction catalysed by L-carnitine hydroxide. This green method yielded products in 75–97% yield. Density functional theory analysis showed that these compounds have favourable HOMO–LUMO gaps and enhanced charge transfer, suggesting good nonlinear optical properties. Molecular docking indicated strong binding to key bacterial proteins. In vitro tests confirmed strong antioxidant activity (DPPH IC<sub>50</sub>: 21.1–49.8&#xa0;µg/mL; NO IC<sub>50</sub>: 21.2–31.1&#xa0;µg/mL) and effective antibacterial action against both Gram-positive and Gram-negative bacteria (inhibition zones: 2.0–3.8&#xa0;mm). The compounds also inhibited cancer cell growth in five human cell lines (IC<sub>50</sub>: 3.5–5.9&#xa0;µM), with higher selectivity than doxorubicin over non-cancerous cells. ADMET analysis predicted good absorption, low toxicity and drug-likeness. Electron-withdrawing groups improved both biological and electronic properties. These phosphonates are promising candidates for new therapeutic development.</p>

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Biocompatible synthesis, computational studies and therapeutic evaluation of a dibutyl (2,2‐dicyano‐1‐phenylethyl) phosphonate derivatives targeting oxidative stress, microbial infection and cancer cells

  • 期刊论文

  • 发表日期：

    2025年8月30日

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  • Sumithra Poreddy,
  • Santhisudha Sarva,
  • Surendra Pothuraju,
  • Mohan Gundluru,
  • Poojitha Bellala,
  • Sunitha Gundubogula,
  • Suresh Reddy Cirandur

摘要

We synthesized a series of dibutyl (2,2-dicyano-1-phenylethyl) phosphonates using a solvent-free, one-pot reaction catalysed by L-carnitine hydroxide. This green method yielded products in 75–97% yield. Density functional theory analysis showed that these compounds have favourable HOMO–LUMO gaps and enhanced charge transfer, suggesting good nonlinear optical properties. Molecular docking indicated strong binding to key bacterial proteins. In vitro tests confirmed strong antioxidant activity (DPPH IC50: 21.1–49.8 µg/mL; NO IC50: 21.2–31.1 µg/mL) and effective antibacterial action against both Gram-positive and Gram-negative bacteria (inhibition zones: 2.0–3.8 mm). The compounds also inhibited cancer cell growth in five human cell lines (IC50: 3.5–5.9 µM), with higher selectivity than doxorubicin over non-cancerous cells. ADMET analysis predicted good absorption, low toxicity and drug-likeness. Electron-withdrawing groups improved both biological and electronic properties. These phosphonates are promising candidates for new therapeutic development.