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Abstract <p><b>Objective:</b> This study aimed to synthesize a series of coumarin–pyrazolo[1,5-<i>a</i>]pyrimidine hybrid compounds and evaluate their potential antibacterial and antibiofilm activities. <b>Methods:</b> In our synthetic approach, a mixture of 3-acetylcoumarin (<b>I</b>) and <i>N</i>,<i>N</i>-dimethylformamide dimethyl acetal (DMF-DMA) was refluxed in toluene to afford the enaminone intermediate (<b>II</b>). Subsequent condensation with 3-aminopyrazoles in the presence of potassium hydrogen sulfate (KHSO<sub>4</sub>) yielded a series of 7-(2-oxo-2<i>H</i>-chromen-3-yl)pyrazolo[1,5-<i>a</i>]pyrimidine derivatives. The structures of the synthesized compounds were confirmed using spectroscopic and analytical techniques, including FT-IR, <sup>1</sup>H, <sup>13</sup>C NMR, and high-resolution mass spectrometry (HRMS). Antibacterial and antibiofilm activities were evaluated against <i>Staphylococcus epidermidis</i> ATCC 35984 and <i>Pseudomonas aeruginosa</i> using MIC, MIC<sub>50</sub> assays, and biofilm formation inhibition studies. <b>Results and Discussion:</b> The synthesized coumarin–pyrazolo[1,5-<i>a</i>]pyrimidine (CPP) hybrids (<b>IVa–IVj</b>) were obtained in high yields (74–92%) within short reaction times (9–18 min). These compounds exhibited significant anti-adhesion and antibiofilm activities against both <i>S. epidermidis</i> and <i>P. aeruginosa</i>. All compounds were tested for their ability to inhibit bacterial cell adhesion to polystyrene surfaces. <b>Conclusions:</b> Hybrids (<b>IVd</b>) and (<b>IVe</b>) demonstrated outstanding and consistent antibiofilm activity against strong biofilm-forming strains, <i>S. epidermidis</i> ATCC 35984 and <i>P. aeruginosa</i>, indicating broad-spectrum efficacy at low concentrations.</p>

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Environmentally Friendly Synthesis of Coumarin–Pyrazolo[1,5-a]pyrimidine Hybrids with Potent Antibacterial and Antibiofilm Activities

  • 期刊论文

  • 发表日期：

    2025年6月3日

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  • T. R. A. Sangma,
  • L. B. Marpna,
  • M. Rymbai,
  • S. Kaping,
  • V. V. Borah,
  • J. N. Vishwakarma

摘要

Abstract

Objective: This study aimed to synthesize a series of coumarin–pyrazolo[1,5-a]pyrimidine hybrid compounds and evaluate their potential antibacterial and antibiofilm activities. Methods: In our synthetic approach, a mixture of 3-acetylcoumarin (I) and N,N-dimethylformamide dimethyl acetal (DMF-DMA) was refluxed in toluene to afford the enaminone intermediate (II). Subsequent condensation with 3-aminopyrazoles in the presence of potassium hydrogen sulfate (KHSO4) yielded a series of 7-(2-oxo-2H-chromen-3-yl)pyrazolo[1,5-a]pyrimidine derivatives. The structures of the synthesized compounds were confirmed using spectroscopic and analytical techniques, including FT-IR, 1H, 13C NMR, and high-resolution mass spectrometry (HRMS). Antibacterial and antibiofilm activities were evaluated against Staphylococcus epidermidis ATCC 35984 and Pseudomonas aeruginosa using MIC, MIC50 assays, and biofilm formation inhibition studies. Results and Discussion: The synthesized coumarin–pyrazolo[1,5-a]pyrimidine (CPP) hybrids (IVa–IVj) were obtained in high yields (74–92%) within short reaction times (9–18 min). These compounds exhibited significant anti-adhesion and antibiofilm activities against both S. epidermidis and P. aeruginosa. All compounds were tested for their ability to inhibit bacterial cell adhesion to polystyrene surfaces. Conclusions: Hybrids (IVd) and (IVe) demonstrated outstanding and consistent antibiofilm activity against strong biofilm-forming strains, S. epidermidis ATCC 35984 and P. aeruginosa, indicating broad-spectrum efficacy at low concentrations.