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

作者：Xiang Wang, Zhiyi Lu, Qiang Liu, Shujun Li, Cyril Tang, Pei Li · 发表于：Russian Journal of General Chemistry · 年份：2025 · DOI：10.1134/s1070363225601760 · 被引用次数：2 · 研究领域：Synthesis of Organic Compounds、Synthesis and biological activity、Multicomponent Synthesis of Heterocycles

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.