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
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
  • [21] Synthesis and Insecticidal Activity of 5-Chloro-N-[4-chloro-2-(substitutedcarbamoyl)-6-methylphenyl]-1-aryl-3(trifluoromethyl)-1H-pyrazole-4-carboxamide
    Zhang Xiu-Lan
    Wang Bao-Lei
    Mao Ming-Zhen
    Xiong Li-Xa
    Yu Shu-Jing
    Li Zheng-Ming
    CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2013, 34 (01): : 96 - 102
  • [22] Synthesis and characterization of novel chalcones linked 3-[1-(3-chlorophenyl)-3-(pyren-1-yl)]-1H-pyrazole moiety
    Khalifa, N. M.
    Al-Omar, M. A.
    Ali, O. M.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2017, 87 (11) : 2699 - 2702
  • [23] Synthesis of Novel 3-Chloropyridin-2-yl-Pyrazole Derivatives and their Insecticidal, Fungicidal Activities and QSAR Study
    Zhang, Ji-Feng
    Liu, Chen
    Ma, Yi
    Wang, Bao-Lei
    Xiong, Li-Xia
    Yu, Shu-Jing
    Li, Zheng-Ming
    LETTERS IN DRUG DESIGN & DISCOVERY, 2013, 10 (06) : 497 - 506
  • [24] One-pot synthesis, structure and structure-activity relationship of novel bioactive diphenyl/diethyl (3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)(arylamino)methylphosphonates
    Wang, Bao-Lei
    Zhu, Hong-Wei
    Li, Zheng-Ming
    Zhang, Xiao
    Yu, Shu-Jing
    Ma, Yi
    Song, Hai-Bin
    PEST MANAGEMENT SCIENCE, 2019, 75 (12) : 3273 - 3281
  • [25] Synthesis and Biological Activities of Novel 3-(((3-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl) methylene)amino)-substituted-benzo[d][1,2,3] triazin-4(3H)-ones
    Zhang, Yan
    Zhu, Hongwei
    Shang, Junfeng
    Wang, Baolei
    Li, Zhengming
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (03) : 861 - 866
  • [26] Synthesis and characterization of novel chalcones linked 3-[1-(3-chlorophenyl)-3-(pyren-1-yl)]-1H-pyrazole moiety
    N. M. Khalifa
    M. A. Al-Omar
    O. M. Ali
    Russian Journal of General Chemistry, 2017, 87 : 2699 - 2702
  • [27] Synthesis and Bioactivities of Novel 1-Phenyl-3-methyl-5-aryloxy-1H-pyrazole-4-carbaldehyde-O-[(2-chloropyridin-5-yl)methyl]oximes
    Dai, Hong
    Shi, Lei
    Zhang, Haijun
    Li, Yongqiang
    Fang, Jianxin
    Shi, Yujun
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2012, 32 (06) : 1060 - 1066
  • [28] Synthesis and Crystal Structure of N-(1,3,4-Thiadiazol-2-yl)-1-[1-(6-chloropyridin-3-yl)methy]-5-methyl-1H-[1,2,3]triazol-4-carboxamide
    陈小保
    李克
    石德清
    结构化学, 2008, (11) : 1389 - 1392
  • [29] Synthesis of Novel 4-[1-(3-Chlorophenyl)-3-(pyren-1-yl)-1H-pyrazol-4-yl]-2-alkyloxy-6-substituted pyridine-3-carbonitriles
    Khalifa, N. M.
    Al-Omar, M. A.
    Taha, M. M.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2017, 87 (12) : 2966 - 2969
  • [30] Synthesis and Crystal Structure of N-(1,3,4-Thiadiazol-2-yl)-1-[1-(6-chloropyridin-3-yl)methy]-5-methyl-1H-[1,2,3]triazol-4-carboxamide
    Chen Xiao-Bao
    Li Ke
    Shi De-Qing
    CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2008, 27 (11) : 1389 - 1392