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Abstract <p>The reaction of <i>N</i>-toluenesulfonyl glycine, DL-valine, and DL-leucine hydrazides with isothio­cyanates gave substituted thiosemicarbazides containing <i>N</i>-Ts-amino acid fragments, which underwent base-catalyzed cyclization to 3,4-substituted 5-sulfanyl-1,2,4-triazoles. The latter were subjected to alkylation and oxidation to the corresponding 5-hydroxy derivatives. The alkylation with propyl bromide, chloroacetamide, and 5-acetyl-2-methoxybenzyl chloride involved both sulfur and nitrogen nucleophilic centers of the triazole derivatives containing a glycine residue and only the sulfur atom of valine and leucine analogues. The synthesized compounds were screened for antibacterial and anti-monoamine oxidase activities, and docking analysis against relevant protein targets was performed.</p>

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Synthesis of Triazoles with Natural Amino Acid Fragments

  • 期刊论文

  • 发表日期：

    2025年1月1日

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  • A. A. Harutyunyan,
  • M. R. Hakobyan,
  • A. S. Sargsyan,
  • A. A. Hambardzumyan,
  • H. M. Stepanyan,
  • A. S. Grigoryan,
  • H. A. Panosyan

摘要

Abstract

The reaction of N-toluenesulfonyl glycine, DL-valine, and DL-leucine hydrazides with isothio­cyanates gave substituted thiosemicarbazides containing N-Ts-amino acid fragments, which underwent base-catalyzed cyclization to 3,4-substituted 5-sulfanyl-1,2,4-triazoles. The latter were subjected to alkylation and oxidation to the corresponding 5-hydroxy derivatives. The alkylation with propyl bromide, chloroacetamide, and 5-acetyl-2-methoxybenzyl chloride involved both sulfur and nitrogen nucleophilic centers of the triazole derivatives containing a glycine residue and only the sulfur atom of valine and leucine analogues. The synthesized compounds were screened for antibacterial and anti-monoamine oxidase activities, and docking analysis against relevant protein targets was performed.