Synthesis, Nematicidal Evaluation, and the Structure-Activity Relationship Study of Aurone Derivatives

被引:2
|
作者
Cao, Xiaofeng [1 ]
Wang, Mingxia [1 ]
Li, Zhong [1 ]
Xu, Xiaoyong [1 ]
机构
[1] East China Univ Sci & Technol, Sch Pharm, Shanghai Key Lab Chem Biol, Shanghai 200237, Peoples R China
基金
中国国家自然科学基金;
关键词
SHAFTS; scaffold hopping; nematicidal activity; aurone derivatives; SAR; INHIBITORY-ACTIVITY; HYBRID APPROACH; DISCOVERY; SHAFTS;
D O I
10.1021/acs.jafc.3c00627
中图分类号
S [农业科学];
学科分类号
09 ;
摘要
Plant-parasitic nematodes (PPNs) are one of the majorthreats tomodern agriculture. Chemical nematicides are still required for themanagement of PPNs. Based on our previous work, the structure of auroneanalogues was obtained using a hybrid 3D similarity calculation method(SHAFTS, SHApe-FeaTure Similarity). Thirty-seven compounds were synthesized.The nematicidal activity of target compounds against Meloidogyne incognita (root-knot nematode, M. incognita) was evaluated, and the structure-activityrelationship of synthesized compounds was analyzed. The results showedthat compound 6 and some of its derivatives exhibitedimpressive nematicidal activity. Among these compounds, compound 32 bearing 6-F showed the best in vitro and in vivo nematicidal activity. Its lethal concentration 50%after exposure to 72 h (LC50/72 h) value was 1.75mg/L, and the inhibition rate reached 97.93% in the sand at 40 mg/L.At the same time, compound 32 also exhibited excellentinhibition on egg hatching and moderate inhibition on the motilityof Caenorhabditis elegans (C. elegans).
引用
收藏
页码:8757 / 8768
页数:12
相关论文
共 50 条
  • [31] Design, Synthesis, Antifungal Evaluation, Structure-Activity Relationship (SAR) Study, and Molecular Docking of Novel Spirotryprostatin A Derivatives
    Ma, Yang-Min
    Miao, Xia
    Jia, Bin
    Sun, Zhao-Yang
    Ma, Si-Yue
    Yan, Cong
    MOLECULES, 2024, 29 (04):
  • [32] Synthesis and biological evaluation of p-carborane bisphenols and their derivatives: Structure-activity relationship for estrogenic activity
    Ogawa, Takumi
    Ohta, Kiminori
    Iijima, Toru
    Suzuki, Tomoharu
    Ohta, Shigeru
    Endo, Yasuyuki
    BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (03) : 1109 - 1117
  • [33] Structure-Activity Relationship of Niclosamide Derivatives
    Tang, Zhonghai
    Acuna, Ulyana Munoz
    Fernandes, Nelson Freitas
    Chettiar, Somsundaram
    Li, Pui-Kai
    De Blanco, Esperanza Carcache
    ANTICANCER RESEARCH, 2017, 37 (06) : 2839 - 2843
  • [34] DESIGN, SYNTHESIS AND STRUCTURE-ACTIVITY RELATIONSHIP STUDY OF PYRILAMINE DERIVATIVES AS HISTONE DEACETYLASE INHIBITORS
    Hiranaka, Seiya
    Arata, Mayumi
    Nakata, Akiko
    Tanaka, Akiko
    Hashizume, Yoshinobu
    Kudo, Norio
    Ito, Akihiro
    Yoshida, Minoru
    Uesato, Shinichi
    Nagaoka, Yasuo
    Sumiyoshi, Takaaki
    HETEROCYCLES, 2020, 101 (02) : 726 - 737
  • [35] Synthesis, evaluation and quantitative structure-activity relationship (QSAR) analysis of Wogonin derivatives as cytotoxic agents
    Bian, Jinlei
    Li, Tinghan
    Weng, Tianwei
    Wang, Jubo
    Chen, Yu
    Li, Zhiyu
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2017, 27 (04) : 1012 - 1016
  • [36] Synthesis, structure-activity relationship and in vitro evaluation of coelenterazine and coelenteramine derivatives as inhibitors of lipid peroxidation
    Burton, M
    De Tollenaere, C
    Cavalier, JF
    Marchand, C
    Dussart, F
    Marchand-Brynaert, J
    Rees, JF
    FREE RADICAL RESEARCH, 2003, 37 (02) : 145 - 158
  • [37] Simple isatin derivatives as free radical scavengers: Synthesis, biological evaluation and structure-activity relationship
    Gang Chen
    Ye Wang
    Xiaojiang Hao
    Shuzhen Mu
    Qianyun Sun
    Chemistry Central Journal, 5
  • [38] Simple isatin derivatives as free radical scavengers: Synthesis, biological evaluation and structure-activity relationship
    Chen, Gang
    Wang, Ye
    Hao, Xiaojiang
    Mu, Shuzhen
    Sun, Qianyun
    CHEMISTRY CENTRAL JOURNAL, 2011, 5
  • [39] Synthesis, leishmanicidal activity, structural descriptors and structure-activity relationship of quinoline derivatives
    Silva, Etyene J. G.
    Bezerra-Souza, Adriana
    Passero, Luiz F. D.
    Laurenti, Marcia D.
    Ferreira, Glaucio M.
    Fujii, Drielli G., V
    Trossini, Gustavo H. G.
    Raminelli, Cristiano
    FUTURE MEDICINAL CHEMISTRY, 2018, 10 (17) : 2069 - 2085
  • [40] Synthesis and Activity of Aurone and Indanone Derivatives
    Wu, Heng
    Zhao, Haiqing
    Lu, Tong
    Xie, Baoxing
    Niu, Chao
    Aisa, Haji Akber
    MEDICINAL CHEMISTRY, 2023, 19 (07) : 686 - 703