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Abstract <p><b>Objective:</b> A green, solvent-free multicomponent synthesis of dibutyl (2-amino-3-cyano-4<i>H</i>-chromen-4-yl)phosphonates was developed using a homopiperazine catalyst under ultrasound irradiation to generate multifunctional scaffolds with therapeutic potential. <b>Methods:</b> Structural stability and electronic properties of the synthesized compounds were evaluated <i>via</i> Density Functional Theory (DFT). Molecular docking was performed against EGFR, HER2, MMP-9, TGFBR1, and VEGFR2, while ADMET modeling assessed pharmacokinetic profiles and toxicity risks. Biological evaluations included antioxidant, antimicrobial, and cytotoxicity assays. <b>Results and Discussion:</b> DFT calculations confirmed molecular stability and favorable reactivity descriptors. Molecular docking revealed potent multitarget binding affinity, particularly for compounds <b>4h</b>, <b>4g</b>, and <b>4b</b>. ADMET analysis indicated promising drug-like profiles with acceptable toxicity. <i>In vitro</i> assays demonstrated potent antioxidant activity, broad-spectrum antimicrobial effects, and significant cytotoxicity against MCF-7, MDA-MB-231, DU-145, HeLa, and HepG2 cell lines. Notably, compounds <b>4h</b>, <b>4g</b>, <b>4b</b>, <b>4l</b>, and <b>4k</b> exhibited superior cytotoxic efficacy compared to doxorubicin. Observed bioactivity correlated with electronic features, including MEP distribution and frontier molecular orbital energies. <b>Conclusions:</b> The integration of green synthesis, computational modeling, and biological validation highlights these chromenyl phosphonate hybrids as promising candidates for multitarget therapeutic applications, including oncology, oxidative stress modulation, and infectious diseases.</p>

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From Green Synthesis to Biological Insight: A Multifaceted Study of Dibutyl (2-amino-3-cyano-4H-chromen-4-yl)phosphonates via DFT, ADMET, Docking, and In Vitro Assays

  • 期刊论文

  • 发表日期：

    2026年5月6日

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

摘要

Abstract

Objective: A green, solvent-free multicomponent synthesis of dibutyl (2-amino-3-cyano-4H-chromen-4-yl)phosphonates was developed using a homopiperazine catalyst under ultrasound irradiation to generate multifunctional scaffolds with therapeutic potential. Methods: Structural stability and electronic properties of the synthesized compounds were evaluated via Density Functional Theory (DFT). Molecular docking was performed against EGFR, HER2, MMP-9, TGFBR1, and VEGFR2, while ADMET modeling assessed pharmacokinetic profiles and toxicity risks. Biological evaluations included antioxidant, antimicrobial, and cytotoxicity assays. Results and Discussion: DFT calculations confirmed molecular stability and favorable reactivity descriptors. Molecular docking revealed potent multitarget binding affinity, particularly for compounds 4h, 4g, and 4b. ADMET analysis indicated promising drug-like profiles with acceptable toxicity. In vitro assays demonstrated potent antioxidant activity, broad-spectrum antimicrobial effects, and significant cytotoxicity against MCF-7, MDA-MB-231, DU-145, HeLa, and HepG2 cell lines. Notably, compounds 4h, 4g, 4b, 4l, and 4k exhibited superior cytotoxic efficacy compared to doxorubicin. Observed bioactivity correlated with electronic features, including MEP distribution and frontier molecular orbital energies. Conclusions: The integration of green synthesis, computational modeling, and biological validation highlights these chromenyl phosphonate hybrids as promising candidates for multitarget therapeutic applications, including oncology, oxidative stress modulation, and infectious diseases.