Novel conjugated 5-alkenyl rhodanine tethered 1,4-benzodioxane derivatives as dual-chitinases inhibitors to hinder the growth of Asian corn borer

文献类型： 外文期刊

第一作者： Chen, Jinxiu

作者： Chen, Jinxiu;Shi, Dongmei;Jiang, Zhiyang;Zou, Renxuan;Zhang, Jingyu;Han, Qing;Wang, Na;Duan, Hongxia;Chen, Jinxiu;Shi, Dongmei;Jiang, Zhiyang;Zou, Renxuan;Zhang, Jingyu;Han, Qing;Wang, Na;Duan, Hongxia;Xu, Zhijian;Yang, Qing

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关键词： O. furnacalis; Chitinase; 5-alkenylthiazolidinone; 1,4-benzodioxane; Dual-chitinases inhibitor

期刊名称：MEDICINAL CHEMISTRY RESEARCH （ 影响因子：3.1； 五年影响因子：2.8 ）

ISSN： 1054-2523

年卷期： 2025 年 34 卷 4 期

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收录情况： SCI

摘要： OfChtI and OfChi-h are ideal targets for developing agricultural inhibitors against Ostrinia furnacalis. In order to further confirm the importance of conjugated systems in rhodanine derivatives, sixteen novel 1,4-benzodioxane-tethered-rhodanine derivatives were designed and synthesized with or without C=C double bond of 5-alkenyl rhodanine skeleton. Among them, compounds 3a-3h, with preserved 5-alkenyl rhodanine skeleton, all exhibited much better inhibitory activities against both OfChtI and OfChi-h, compared to that of the corresponding reduced compounds 4a-4h without its C=C double bond. The inhibitory mechanism demonstrated that the 5-alkenyl rhodanine conjugated plane was conducive to improving the binding affinity with both two chitinases. Compound 3g was identified as the most potential dual-chitinases inhibitor against OfChtI (K-i=2.57 mu M) and OfChi-h (K-i=2.03 mu M). The bioassay study also indicated that compound 3g displayed the best insecticidal activity against O. furnacalis and distinctive sublethal effect in regulating its growth and development. These 1,4-benzodioxane-tethered-rhodanine derivatives deserved further investigation as novel dual-chitinases inhibitor candidates in the control of O. furnacalis. [GRAPHICS] .

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