数字农科院2.0

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

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

作者机构：

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

期刊名称： MEDICINAL CHEMISTRY RESEARCH

ISSN： 1054-2523

年卷期： 2025 年

页码：

收录情况： SCIE（2025版）

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 (Ki = 2.57 mu M) and OfChi-h (Ki = 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.

分类号：

  • 相关文献

[1]High-yield production of a chitinase from Aeromonas veronii B565 as a potential feed supplement for warm-water aquaculture. Zhang, Yuting,Zhou, Zhigang,Liu, Yuchun,Cao, Yanan,He, Suxu,Huo, Fengmin,Qin, Chubin,Yao, Bin,Ringo, Einar.

[2]Microbial Secondary Metabolite, Phlegmacin B-1, as a Novel Inhibitor of Insect Chitinolytic Enzymes. Liu, Tian,Duan, Yanwei,Yang, Qing,Chen, Lei,Liu, Tian,Duan, Yanwei,Yang, Qing,Liu, Tian,Yang, Qing,Lu, Xinhua.

[3]Microbial diversity in the sediment of a crab pond in Nanjing, China. Liu, Yuchun,Zhou, Zhigang,He, Suxu,Yao, Bin,Ringo, Einar. 2013

[4]Production of N-Acetyl-D-glucosamine from Mycelial Waste by a Combination of Bacterial Chitinases and an Insect N-Acetyl-D-glucosaminidase. Wang, Di,Liu, Tian,Yang, Qing,Zhu, Weixing,Wang, Di,Liu, Tian,Yang, Qing,Yang, Qing.

[5]The expression of a baculovirus-derived chitinase gene increased resistance of tobacco cultivars to brown spot (Alternaria alternata). Shi, J,Thomas, CJ,King, LA,Hawes, CR,Possee, RD,Edwards, ML,Pallett, D,Cooper, JI. 2000

[6]Microbial Secondary Metabolite, Phlegmacin B-1, A.s A Novel Inhibitor O f Insect Chitinolytic Enzymes. Lu, Xinhua,Yang, Qing,Yang, Qing,Liu, Tian,Chen, Lei,Duan, Yanwei,Liu, Tian. 2017

[7]Pocket-Based Lead Optimization Strategy For T.he Design And Synthesis O f Chitinase Inhibitors. Dong, Yawen,He, Xiongkui,Hu, Song,Jiang, Xi,Ling, Yun,Liu, Tian,Yang, Qing,Yang, Qing,Zhang, Li. 2019

[8]Biological Characteristics of Recombinant Arthrobotrys oligospora Chitinase AO-801. Gong S.,Meng Q.,Qiao J.,Huang Y.,Zhong W.,Zhang G.,Zhang K.,Li N.,Shang Y.,Li Z.,Cai X.. 2022

[9]Discovery of Azo-Aminopyrimidines as Novel and Potent Chitinase O fChi-h Inhibitors via Structure-Based Virtual Screening and Rational Lead Optimization. Lili Dong,Shengqiang Shen,Xi Jiang,Yaxin Liu,Jingjing Li,Wei Chen,Yizhen Wang,Jiakun Shi,Jiaxin Liu,Shujie Ma,Lihui Zhang,Jingao Dong,Qing Yang. 2022

[10]Discovery of Kasugamycin as a Potent Inhibitor of Glycoside Hydrolase Family 18 Chitinases. Qi Huitang,Jiang Xi,Ding Yi,Liu Tian,Yang Qing. 2021

[11]Novel Inhibitors of an Insect Pest Chitinase: Design and Optimization of 9-O-Aromatic and Heterocyclic Esters of Berberine. Ling Zhu,Lei Chen,Xusheng Shao,Jiagao Cheng,Qing Yang,Xuhong Qian. 2021

[12]Heterologous expression and characterization of thermostable chitinase and β-N-acetylhexosaminidase from Caldicellulosiruptor acetigenus and their synergistic action on the bioconversion of chitin into N-acetyl-D-glucosamine. Xing Qin,Yan Zhe Xin,Xiaoyun Su,Xiaolu Wang,Jie Zhang,Tao Tu,Yaru Wang,Bin Yao,Huoqing Huang,Huiying Luo. 2021

[13]Insect group II chitinase OfChtII promotes chitin degradation during larva–pupa molting. Ming-Bo Qu,Shao-Peng Sun,Yuan-Sheng Liu,Xiao-Rui Deng,Jun Yang,Qing Yang. 2021

[14]Discovery of aromatic 2-(3-(methylcarbamoyl) guanidino)-N-aylacetamides as highly potent chitinase inhibitors. Zhao Z.,Li F.,Chen W.,Yang Q.,Lu H.,Zhang J.. 2023

[15]Discovery of Potent N-Methylcarbamoylguanidino Insect Growth Regulators Targeting OfChtI and OfChi-h. Zhao, Zhixiang,Chen, Wei,Dong, Yanhong,Yang, Qing,Lu, Huizhe,Zhang, Jianjun. 2023

[16]Structural and biochemical insights into an insect gut-specific chitinase with antifungal activity. 杨青. 2020

[17]A novel thermophilic chitinase directly mined from the marine metagenome using the deep learning tool Preoptem. Zhang, Yan,Guan, Feifei,Xu, Guoshun,Liu, Xiaoqing,Zhang, Yuhong,Sun, Jilu,Yao, Bin,Huang, Huoqing,Wu, Ningfeng,Tian, Jian. 2022

[18]Discovery of Kasugamycin as a Potent Inhibitor of Glycoside Hydrolase Family 18 Chitinases. Qi Huitang,Jiang Xi,Ding Yi,Liu Tian,Yang Qing. 2021

[19]Rational Design, Synthesis, and Biological Investigations of N-Methylcarbamoylguanidinyl Azamacrolides as a Novel Chitinase Inhibitor. Zhixiang Zhao,Qingbo Xu,Wei Chen,Siming Wang,Qing Yang,Yanhong Dong,Jianjun Zhang. 2022

[20]Structure-Based Virtual Screening of Natural Products and Optimization for the Design and Synthesis of Novel CeCht1 Inhibitors as Nematicide Candidates. Jin, Xiaoyu,Sun, Tengda,Zhang, Xiaoming,Guo, Bingbo,Cui, Jialin,Ling, Yun,Zhang, Li,Yang, Qing,Chen, Wei,Yang, Xinling. 2023

作者其他论文 更多>>