<p>A novel series of amino ester-modified juglone derivatives was synthesized via cerium trichloride-catalyzed addition and oxidation reactions between 5-hydroxynaphthalene-1,4-dione (juglone) and various amino acid methyl esters. The antimicrobial activities of the synthesized compounds were systematically evaluated against <i>Escherichia coli</i> and <i>Staphylococcus aureus</i> using inhibition zone and absorbance-based assays. The results indicated that the nature of the amino acid substituent significantly affected antibacterial performance, with derivatives containing valine, leucine, and threonine groups showing enhanced inhibitory effects. In particular, strong growth suppression was observed against <i>S. aureus</i>, suggesting a notable structure–activity relationship influenced by steric and chiral factors. These findings demonstrate the potential of amino acid-functionalized juglones as promising scaffolds for developing new antimicrobial agents.</p> Graphical Abstract <p></p>

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Design, synthesis, and antibacterial evaluation of amino ester-modified juglone derivatives

  • Shaohong Zeng,
  • Said Alam,
  • Yanxia Mao,
  • Liang Chen,
  • Hongfei Lu,
  • Chunhui Jiang

摘要

A novel series of amino ester-modified juglone derivatives was synthesized via cerium trichloride-catalyzed addition and oxidation reactions between 5-hydroxynaphthalene-1,4-dione (juglone) and various amino acid methyl esters. The antimicrobial activities of the synthesized compounds were systematically evaluated against Escherichia coli and Staphylococcus aureus using inhibition zone and absorbance-based assays. The results indicated that the nature of the amino acid substituent significantly affected antibacterial performance, with derivatives containing valine, leucine, and threonine groups showing enhanced inhibitory effects. In particular, strong growth suppression was observed against S. aureus, suggesting a notable structure–activity relationship influenced by steric and chiral factors. These findings demonstrate the potential of amino acid-functionalized juglones as promising scaffolds for developing new antimicrobial agents.

Graphical Abstract