<p>Pseudo-peptides are an important category of biologically active artificial small molecules. To access these important molecules, a novel series of bisazlactones was synthesized via the Erlenmeyer-Plöchl reaction, using glycine- and terephthaloyl-based diacid with aldehydes. These bisazlactones were then utilized as efficient intermediates in reactions with primary and secondary amines, providing novel pseudo-peptides containing enamide groups in high to excellent yields. The selected pseudo-peptide enamides exhibited selective cytotoxicity against hepatocarcinoma cells, while exhibiting negligible impact on normal mammalian cells. Notably, compound <b>6y</b> displayed superior anti-cancer activity compared to the others.</p>

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Synthesis of novel bisazlactones and their applications in the synthesis of a new family of pseudo-peptide enamides with anti-cancer properties

  • Azim Ziyaei Halimehjani,
  • Farzaneh Noorakhtar

摘要

Pseudo-peptides are an important category of biologically active artificial small molecules. To access these important molecules, a novel series of bisazlactones was synthesized via the Erlenmeyer-Plöchl reaction, using glycine- and terephthaloyl-based diacid with aldehydes. These bisazlactones were then utilized as efficient intermediates in reactions with primary and secondary amines, providing novel pseudo-peptides containing enamide groups in high to excellent yields. The selected pseudo-peptide enamides exhibited selective cytotoxicity against hepatocarcinoma cells, while exhibiting negligible impact on normal mammalian cells. Notably, compound 6y displayed superior anti-cancer activity compared to the others.