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
  • [31] Synthesis and Herbicidal Activity of Novel 1-(Diethoxyphosphoryl)-3-(4-one-1H-1,2,3-triazol-1-yl)-propan-2-yl Carboxylic Esters
    Jin, Yan
    Zhao, Hanqing
    Lu, Huizhe
    Kuemmel, Colleen M.
    Zhang, Jianjun
    Wang, Daoquan
    MOLECULES, 2015, 20 (01) : 1088 - 1103
  • [32] The Discovery of 3-((4-Chloro-3-methoxyphenyl)amino)-1-((3R,4S)-4-cyanotetrahydro-2H-pyran-3-yl)-1H-pyrazole-4-carboxamide, a Highly Ligand Efficient and Efficacious Janus Kinase 1 Selective Inhibitor with Favorable Pharmacokinetic Properties
    Siu, Tony
    Brubaker, Jason
    Fuller, Peter
    Torres, Luis
    Zeng, Hongbo
    Close, Joshua
    Mampreian, Dawn M.
    Shi, Feng
    Liu, Duan
    Fradera, Xavier
    Johnson, Kevin
    Bays, Nathan
    Kadic, Elma
    He, Fang
    Goldenblatt, Peter
    Shaffer, Lynse
    Patel, San Ita B.
    Lesburg, Charles A.
    Alpert, Carla
    Dorosh, Lauren
    Deshmukh, Sujal V.
    Yu, Hongshi
    Klappenbach, Joel
    Elwood, Fiona
    Dinsmore, Christopher J.
    Fernandez, Rafael
    Moy, Lily
    Young, Jonathan R.
    JOURNAL OF MEDICINAL CHEMISTRY, 2017, 60 (23) : 9676 - 9690
  • [33] Synthesis and Biological Activities of Novel N-(2-(5-(3-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)-1,3,4-oxadiazol-2-yl)-4-chloro-6-methylphenyl) Amides
    Zhang, Yan
    Shang, Junfeng
    Li, Huan
    Liu, Hang
    Song, Haibin
    Wang, Baolei
    Li, Zhengming
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (03) : 787 - 793
  • [34] Synthesis of some new pyrazolyl-thiazolidinone derivatives starting from 1-(3-chlorophenyl)-3-(4-methoxyphenyl)-1H-pyrazole-4-carboxaldehyde
    Khalifa, N. M.
    Nossier, E. S.
    Al-Omar, M. A.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2017, 87 (04) : 868 - 872
  • [35] Synthesis, Crystal Structure and Biological Activity of 2-Chloro-5-(((5-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)-4-phenyl-4H-1,2,4-triazol-3-yl)thio)methyl)thiazole
    Shen Zhong-Hua
    Zhai Zhi-Wen
    Sun Zhao-Hui
    Weng Jian-Quan
    Tan Cheng-Xia
    Liu Xing-Hai
    CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2017, 36 (07) : 1137 - 1141
  • [36] Synthesis and Antitumor Studies of Acylhydrazone and Hydrazone Derivatives Bearing 3-(1H-indol-3-yl)-1H-pyrazole Scaffold
    Zhang, Datong
    Xu, Rongrong
    Guo, Shoudong
    REVISTA DE CHIMIE, 2014, 65 (06): : 644 - 648
  • [37] Synthesis, Crystal Structure, Antitumor Activities and Docking Study of 1-(2-(1H-Indol-3-yl)ethyl)-3-(2-methoxyphenyl)urea
    Hu Chun-Hong
    Wei Dui-Dui
    Sun Xiao-Fei
    Lin Rui-Li
    Hu Min-Min
    Tang Lei
    Wang Zhen
    He Dian
    CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2018, 37 (03) : 393 - 399
  • [38] Synthesis, in silico Molecular Docking and Antimicrobial Study of Some New 3-(Substituted-quinolin-3-yl)-1-[4-(1H-pyrrol-1-yl)phenyl]prop-2-en-1-one Derivatives
    Kumar, S. R. Prem
    Alshabi, Ali Mohamed
    Shaikh, Ibrahim Ahmed
    Almehizia, Abdulrahman A.
    Kulkarni, Venkatarao H.
    Joshi, Shrinivas D.
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2021, 31 (01) : 91 - 100
  • [39] Synthesis and antifungal activity of novel (1-arylmethyl-3-aryl-1H-pyrazol-5-yl)(4-arylpiperazin-1-yl) methanone derivatives
    Lv, Hong-Shui
    Wang, Li-Ying
    Ding, Xiao-Ling
    Wang, Xiu-Hua
    Zhao, Bao-Xiang
    Zuo, Hua
    JOURNAL OF CHEMICAL RESEARCH, 2013, (08) : 473 - 475
  • [40] Synthesis, Crystal Structure, Herbicidal Activity and Docking Study of 4-Cyclopropyl-3-((4-fluorobenzyl)sulfonyl)-5-methyl-4H-1,2,4-triazole
    Min Li-Jing
    Qiao Li
    Wang Han
    Han Liang
    Liu Xing-Hai
    CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2019, 38 (08) : 1356 - 1361
12345