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<p>This study presents a sustainable one-pot synthesis of novel pyrazolyl phosphonate derivatives via a three-component reaction using 3-methyl-1-phenyl-2-pyrazoline-5-one, aryl aldehydes and dibutyl phosphite, catalyzed by thiamine hydrochloride under solvent-free conditions. Two of these synthetic chemicals were chosen for in-depth density functional theory analysis due to their electron-donating (methoxy) and electron-withdrawing (nitro) groups, providing insights into their electronic properties, reactivity and stability through highest occupied molecular orbital-lowest unoccupied molecular orbital energy gap calculations. Strong interactions with the active sites of acetylcholinesterase (AChE) were found by molecular docking experiments. The compounds also exhibited potent anti-inflammatory and antioxidant activities in biological assays. Additionally, absorption, distribution, metabolism, excretion and toxicity profiling suggested favourable bioavailability and low toxicity, demonstrating their medicinal potential in the creation of new drugs.</p> Graphical abstract <p></p>

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Sustainable one-pot synthesis, digital ADMET modelling, DFT analysis, molecular docking and biological screening of dibutyl((5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)(aryl)methyl) phosphonates

  • 期刊论文

  • 发表日期：

    2025年4月24日

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

摘要

This study presents a sustainable one-pot synthesis of novel pyrazolyl phosphonate derivatives via a three-component reaction using 3-methyl-1-phenyl-2-pyrazoline-5-one, aryl aldehydes and dibutyl phosphite, catalyzed by thiamine hydrochloride under solvent-free conditions. Two of these synthetic chemicals were chosen for in-depth density functional theory analysis due to their electron-donating (methoxy) and electron-withdrawing (nitro) groups, providing insights into their electronic properties, reactivity and stability through highest occupied molecular orbital-lowest unoccupied molecular orbital energy gap calculations. Strong interactions with the active sites of acetylcholinesterase (AChE) were found by molecular docking experiments. The compounds also exhibited potent anti-inflammatory and antioxidant activities in biological assays. Additionally, absorption, distribution, metabolism, excretion and toxicity profiling suggested favourable bioavailability and low toxicity, demonstrating their medicinal potential in the creation of new drugs.

Graphical abstract