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<p>This study focuses on the synthesis, characterization, and evaluation of two novel pyrazole-based ligands, 2-(((3,5-dimethyl-1<i>H</i>-pyrazole-1-yl)methyl)amino)phenol <b>L1</b> and 2-(bis((3,5-dimethyl-1<i>H</i>-pyrazole-1-yl)methyl)amino)phenol <b>L2</b>, and their corresponding copper(II) complexes. The ligands were synthesized through a multi-step alkylation process and complexed with copper(II) chloride to form six coordination complexes, <b>CL1-1</b>, <b>CL1-2</b>, <b>CL1-3</b> for <b>L1</b>, and <b>CL2-1</b>, <b>CL2-2</b>, <b>CL2-3</b> for <b>L2</b>. Structural characterization was performed using NMR, UV–Vis, and FT-IR spectroscopy, confirming the successful formation of the ligands and complexes. Biological evaluation revealed significant anticancer activity, with <b>L1</b> exhibiting potent cytotoxicity against HCT116 colon cancer cells (IC<sub>50</sub> = 13.28 ± 0.63&#xa0;µM) and <b>L2</b> showing selectivity toward SH-SY5Y brain cancer cells (IC<sub>50</sub> = 22.01 ± 0.89&#xa0;µM). Both ligands demonstrated moderate antibacterial activity against <i>Escherichia coli</i>, <i>Staphylococcus aureus</i>, and <i>Pseudomonas aeruginosa</i>, while <b>L2</b> exhibited strong antifungal activity against <i>Candida glabrata</i> (inhibition zone = 23.63&#xa0;mm), outperforming the reference drug caspofungin. ADME studies provided insights into the pharmacokinetic profiles, indicating favorable drug-like properties for some complexes. Catalytic studies demonstrated the efficiency of the copper(II) complexes in the oxidation of 2,6-dimethylphenol, with the <b>CL1-2</b> complex showing the highest catalytic activity. This work highlights the dual potential of pyrazole derivatives as both therapeutic agents and catalysts, bridging the fields of medicinal and coordination chemistry.</p> Graphical Abstract <p></p>

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Synthesis, characterization, and dual applications of novel pyrazole-based ligands and their copper(II) complexes: anticancer, antimicrobial, and catalytic properties

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2025年12月30日

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  • Islam Qorri,
  • El Mehdi Haily,
  • Zakariae Abbaoui,
  • Aziz Boulouiz,
  • Rachid Touzani,
  • Hüseyin Karci,
  • İlknur Özdemir,
  • Nevin Gürbüz,
  • Ismail Ozdomir

摘要

This study focuses on the synthesis, characterization, and evaluation of two novel pyrazole-based ligands, 2-(((3,5-dimethyl-1H-pyrazole-1-yl)methyl)amino)phenol L1 and 2-(bis((3,5-dimethyl-1H-pyrazole-1-yl)methyl)amino)phenol L2, and their corresponding copper(II) complexes. The ligands were synthesized through a multi-step alkylation process and complexed with copper(II) chloride to form six coordination complexes, CL1-1, CL1-2, CL1-3 for L1, and CL2-1, CL2-2, CL2-3 for L2. Structural characterization was performed using NMR, UV–Vis, and FT-IR spectroscopy, confirming the successful formation of the ligands and complexes. Biological evaluation revealed significant anticancer activity, with L1 exhibiting potent cytotoxicity against HCT116 colon cancer cells (IC50 = 13.28 ± 0.63 µM) and L2 showing selectivity toward SH-SY5Y brain cancer cells (IC50 = 22.01 ± 0.89 µM). Both ligands demonstrated moderate antibacterial activity against Escherichia coli, Staphylococcus aureus, and Pseudomonas aeruginosa, while L2 exhibited strong antifungal activity against Candida glabrata (inhibition zone = 23.63 mm), outperforming the reference drug caspofungin. ADME studies provided insights into the pharmacokinetic profiles, indicating favorable drug-like properties for some complexes. Catalytic studies demonstrated the efficiency of the copper(II) complexes in the oxidation of 2,6-dimethylphenol, with the CL1-2 complex showing the highest catalytic activity. This work highlights the dual potential of pyrazole derivatives as both therapeutic agents and catalysts, bridging the fields of medicinal and coordination chemistry.

Graphical Abstract