Halimehjani Azim Ziyaei, Noorakhtar Farzaneh
Department of Chemistry, Sharif University of Technology, Tehran, 11155-9516, Iran.
Faculty of Chemistry, Kharazmi University, 49 Mofateh St, Tehran, 15719-14911, Iran.
Amino Acids. 2025 May 27;57(1):31. doi: 10.1007/s00726-025-03459-0.
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.
伪肽是一类重要的具有生物活性的人工小分子。为了获得这些重要分子，通过厄伦迈尔-普勒赫尔反应，使用基于甘氨酸和对苯二甲酰基的二酸与醛合成了一系列新型双氮杂环丁二酮。然后将这些双氮杂环丁二酮用作与伯胺和仲胺反应的有效中间体，以高至优异的产率提供含有烯酰胺基团的新型伪肽。所选的伪肽烯酰胺对肝癌细胞表现出选择性细胞毒性，而对正常哺乳动物细胞的影响可忽略不计。值得注意的是，化合物6y与其他化合物相比表现出卓越的抗癌活性。
