Synthesis, nematocidal activity and docking study of novel chiral 1-(3-chloropyridin-2-yl)-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide derivatives

被引：87
|
作者：
Liu, Xing-Hai [1 ]
Zhao, Wen [1 ,2 ]
Shen, Zhong-Hua [1 ]
Xing, Jia-Hua [2 ]
Yuan, Jing [2 ]
Yang, Guo [1 ]
Xu, Tian-Ming [2 ]
Peng, Wei-Li [2 ]
机构：
[1] Zhejiang Univ Technol, Coll Chem Engn, Hangzhou 310014, Zhejiang, Peoples R China
[2] Zhejiang Res Inst Chem Ind, Zhejiang Base Natl Southern Pesticide Res Ctr, Hangzhou 310023, Zhejiang, Peoples R China
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2016年 / 26卷 / 15期
关键词：
Trifluoromethylpyrazole; Chiral chain; Nematocidal activity; Synthesis; Docking; ONE-POT SYNTHESIS; MICROWAVE-ASSISTED SYNTHESIS; DIMERIC CRYSTAL-STRUCTURE; ANTIFUNGAL ACTIVITY; 1,2,3-THIADIAZOLE DERIVATIVES; BIOLOGICAL-ACTIVITIES; EFFICIENT SYNTHESIS; DESIGN; MOIETY; 1,3,4-THIADIAZOLE;
D O I：
10.1016/j.bmcl.2016.06.004
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
A series of novel chiral fluorinated pyrazole carboxamides derivatives were designed and synthesized. All these title compounds were confirmed by NMR and MS. The primarily nematocidal activity results indicated that some of them exhibited good control efficacy against the tomato root-knot nematode disease caused by Meloidogyne incognita. The docking results indicated that compound 5n interact with amino acid residue Tyr 121, Trp 279 of AchE via hydrogen bond. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3626 / 3628
页数：3
相关论文
共 50 条
  • [1] Synthesis and nematocidal activity of novel 1-(3-chloropyridin-2-yl)-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide derivatives
    Wen Zhao
    Zhong-Hua Shen
    Jia-Hua Xing
    Guo Yang
    Tian-Ming Xu
    Wei-Li Peng
    Xing-Hai Liu
    Chemical Papers, 2017, 71 : 921 - 928
  • [2] Synthesis and nematocidal activity of novel 1-(3-chloropyridin-2-yl)-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide derivatives
    Zhao, Wen
    Shen, Zhong-Hua
    Xing, Jia-Hua
    Yang, Guo
    Xu, Tian-Ming
    Peng, Wei-Li
    Liu, Xing-Hai
    CHEMICAL PAPERS, 2017, 71 (05): : 921 - 928
  • [3] Synthesis, Nematocidal Activity and Docking Study of Novel Chiral 1-(3-Chloropyridin-2-yl)-3-(difluoromethyl)-1H-pyrazole-4-carboxamide Derivatives
    Zhao, Wen
    Shen, Zhong-Hua
    Xu, Tian-Ming
    Peng, Wei-Li
    Liu, Xing-Hai
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (03) : 1751 - 1756
  • [4] Synthesis and in vivo nematocidal evaluation of novel 3-(trifluoromethyl)-1H-pyrazole-4-carboxamide derivatives
    Zhao, Wen
    Xing, Jiahua
    Xu, Tianming
    Peng, Weili
    Liu, Xinghai
    FRONTIERS OF CHEMICAL SCIENCE AND ENGINEERING, 2017, 11 (03) : 363 - 368
  • [5] Synthesis and in vivo nematocidal evaluation of novel 3-(trifluoromethyl)-1H-pyrazole-4-carboxamide derivatives
    Wen Zhao
    Jiahua Xing
    Tianming Xu
    Weili Peng
    Xinghai Liu
    Frontiers of Chemical Science and Engineering, 2017, 11 : 363 - 368
  • [6] Synthesis and Bioactivities of Novel 1-(3-Chloropyridin-2-yl)-N-Substituted-5-(Trifluoromethyl)-Pyrazole Carboxamide Derivatives
    Wu, Zhibing
    Wu, Shixi
    Ye, Yiqiang
    Zhou, Xiang
    Wang, Peiyi
    Xue, Wei
    Hu, Deyu
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (01) : 325 - 330
  • [7] Design, Synthesis and Antifungal Evaluation of N-Substituted-1-(3-chloropyridin-2-yl)-N-(pyridin-4-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide Derivatives
    Wu, Zhibing
    Yang, Guangqian
    Zhao, Xin
    Wu, Jiangchun
    Wu, Shixi
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2019, 56 (01) : 234 - 238
  • [8] 1-(3-Chloropyridin-2-yl)hydrazine
    Wang, Peng
    Wan, Rong
    Yu, Peng
    He, Qiu
    Zhang, Jian-qiang
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O2599 - U808
  • [9] Synthesis and Antifungal Activity of N-(Substituted pyridinyl)-1-methyl(phenyl)-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide Derivatives
    Wu, Zhibing
    Hu, Deyu
    Kuang, Jiqing
    Cai, Hua
    Wu, Shixi
    Xue, Wei
    MOLECULES, 2012, 17 (12): : 14205 - 14218
  • [10] Synthesis and insecticidal activity of diacylhydrazine derivatives containing a 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole scaffold
    Yanyan Wang
    Fangzhou Xu
    Gang Yu
    Jun Shi
    Chuanhui Li
    A’li Dai
    Zhiqian Liu
    Jiahong Xu
    Fenghua Wang
    Jian Wu
    Chemistry Central Journal, 11
12345