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Abstract <p>Herein, a series of novel 4-chromanone-derived compounds incorporating an oxime ether moiety were synthesized and their structures were confirmed using <sup>1</sup>H, <sup>13</sup>C NMR, and HRMS methods. Bioassay results demonstrated that some of the target compounds exhibited moderate to good antibacterial activities against <i>Xanthomonas oryzae</i> pv. <i>oryzae</i> (<i>Xoo</i>), <i>Xanthomonas campestris</i> (<i>Xac</i>), and <i>Pseudocercospora actinidiae</i> (<i>Psa</i>), as well as antifungal activities against <i>Fusarium oxysporum</i> (<i>F. oxysporum</i>), <i>Gibperella zeae</i> (<i>G. zeae</i>), <i>Sclerotinia sclerotiorum</i> (<i>S. sclerotiorum</i>), <i>Botrytis cinerea</i> (<i>B. cinerea</i>), <i>Verticillium dahliae</i> (<i>V. dahliaee</i>), and <i>Pellicularia sasakii</i> (<i>P. sasakii</i>). Particularly, compound ethyl (<i>E</i>)-6-chloro-4-(methoxyimino)chromane-2-carboxylate was found to exhibit excellent antibacterial activities against <i>Xoo</i> and <i>Psa</i>, with the EC<sub>50</sub> values of 22.04 and 16.87 μg/mL, respectively, surpassing those of bismerthiazol. In addition, compound isopropyl (<i>E</i>)-6-chloro-4-(ethoxyimino)chromane-2-carboxylate demonstrated excellent antifungal activity against <i>B. cinerea</i> at 50 μg/mL, achieving an inhibition rate of 65.30%, which surpassed carbendazol (38.30%) and was comparable to hymexazol (67.30%). To our knowledge, this is the first report on the antibacterial and antifungal activities of this series of novel 4-chromanone-derived compounds incorporating an oxime ether moiety.</p>

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Design, Synthesis, and Biological Evaluation of Novel 4-Chromanone-Derived Compounds Incorporating an Oxime Ether Moiety

  • 期刊论文

  • 发表日期：

    2025年6月1日

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  • X. Wang,
  • Z. Lu,
  • Q. Liu,
  • S. Li,
  • C. Tang,
  • P. Li

摘要

Abstract

Herein, a series of novel 4-chromanone-derived compounds incorporating an oxime ether moiety were synthesized and their structures were confirmed using 1H, 13C NMR, and HRMS methods. Bioassay results demonstrated that some of the target compounds exhibited moderate to good antibacterial activities against Xanthomonas oryzae pv. oryzae (Xoo), Xanthomonas campestris (Xac), and Pseudocercospora actinidiae (Psa), as well as antifungal activities against Fusarium oxysporum (F. oxysporum), Gibperella zeae (G. zeae), Sclerotinia sclerotiorum (S. sclerotiorum), Botrytis cinerea (B. cinerea), Verticillium dahliae (V. dahliaee), and Pellicularia sasakii (P. sasakii). Particularly, compound ethyl (E)-6-chloro-4-(methoxyimino)chromane-2-carboxylate was found to exhibit excellent antibacterial activities against Xoo and Psa, with the EC50 values of 22.04 and 16.87 μg/mL, respectively, surpassing those of bismerthiazol. In addition, compound isopropyl (E)-6-chloro-4-(ethoxyimino)chromane-2-carboxylate demonstrated excellent antifungal activity against B. cinerea at 50 μg/mL, achieving an inhibition rate of 65.30%, which surpassed carbendazol (38.30%) and was comparable to hymexazol (67.30%). To our knowledge, this is the first report on the antibacterial and antifungal activities of this series of novel 4-chromanone-derived compounds incorporating an oxime ether moiety.