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<p>This study investigated the use of commercial chitosan as a simple, eco-friendly, and efficient organocatalyst for the synthesis of xanthene and tetraketone derivatives via a cascade reaction. The reaction between various salicylaldehydes and dimedone (1:2 molar ratio), conducted in water at 75&#xa0;°C, and catalyzed by chitosan, produced xanthene derivatives (<b>3a–g</b>) in good to excellent isolated yields (73–93%) within short reaction times (10–60&#xa0;min). When benzaldehyde was employed as the aldehyde component, tetraketone derivatives (<b>5a–g</b>) were formed instead of xanthene derivatives. A series of substituted benzaldehydes were also investigated, efficiently affording the corresponding Tetraketone derivatives in high yields (82–94%) and short reaction times (10–20&#xa0;min). The reusability of chitosan was confirmed, with no significant decrease in catalytic activity or structural integrity after six consecutive cycles. The synthesized compounds were evaluated for their cytotoxic activity against K-562, A-549, and HCT-116 tumor cell lines, as well as the non-tumor cells MRC-5. Xanthene derivatives demonstrated superior activity, particularly compound <b>3f</b>, which exhibited low IC<sub>50</sub> value for HCT-116 (5.54&#xa0;µM) and SI of 0.54 (SI = IC<sub>50 (MRC-5)</sub>/IC<sub>50 (HCT-116)</sub>). These findings indicate the potential of these molecules as anticancer agents, while also highlighting the need for further structural optimization to enhance selectivity, especially against colon cancer cells.</p> Graphical abstract <p></p>

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Synthesis and evaluation of the cytotoxic activity in tumor cells of xanthene and tetraketone derivatives obtained via cascade reaction using chitosan as an organocatalyst

  • 期刊论文

  • 发表日期：

    2025年11月19日

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  • Paloma G. Abrantes,
  • Poliana G. Abrantes,
  • Renata R. Magalhães,
  • Felipe S. C. Colaço,
  • Yuri V. Santos,
  • Gardenia C. G. Militão,
  • Ercules E. S. Teotônio,
  • Juliana A. Vale

摘要

This study investigated the use of commercial chitosan as a simple, eco-friendly, and efficient organocatalyst for the synthesis of xanthene and tetraketone derivatives via a cascade reaction. The reaction between various salicylaldehydes and dimedone (1:2 molar ratio), conducted in water at 75 °C, and catalyzed by chitosan, produced xanthene derivatives (3a–g) in good to excellent isolated yields (73–93%) within short reaction times (10–60 min). When benzaldehyde was employed as the aldehyde component, tetraketone derivatives (5a–g) were formed instead of xanthene derivatives. A series of substituted benzaldehydes were also investigated, efficiently affording the corresponding Tetraketone derivatives in high yields (82–94%) and short reaction times (10–20 min). The reusability of chitosan was confirmed, with no significant decrease in catalytic activity or structural integrity after six consecutive cycles. The synthesized compounds were evaluated for their cytotoxic activity against K-562, A-549, and HCT-116 tumor cell lines, as well as the non-tumor cells MRC-5. Xanthene derivatives demonstrated superior activity, particularly compound 3f, which exhibited low IC50 value for HCT-116 (5.54 µM) and SI of 0.54 (SI = IC50 (MRC-5)/IC50 (HCT-116)). These findings indicate the potential of these molecules as anticancer agents, while also highlighting the need for further structural optimization to enhance selectivity, especially against colon cancer cells.

Graphical abstract