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

A novel series of chiral fluorinated pyrazole carboxamides derivatives were designed and synthesized. The nematocidal activity was determined. Some of them exhibited good activity. Structure–activity relationship was carried out by docking. [Display omitted] A series of novel chiral fluorinated pyra...

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Published in:Bioorganic & medicinal chemistry letters 2016-08, Vol.26 (15), p.3626-3628
Main Authors: Liu, Xing-Hai, Zhao, Wen, Shen, Zhong-Hua, Xing, Jia-Hua, Yuan, Jing, Yang, Guo, Xu, Tian-Ming, Peng, Wei-Li
Format: Article
Language:English
Subjects:
Animals
Antinematodal Agents - chemical synthesis
Antinematodal Agents - chemistry
Antinematodal Agents - pharmacology
Chiral chain
Docking
Dose-Response Relationship, Drug
Molecular Docking Simulation
Molecular Structure
Nematocidal activity
Pyrazoles - chemical synthesis
Pyrazoles - chemistry
Pyrazoles - pharmacology
Structure-Activity Relationship
Synthesis
Trifluoromethylpyrazole
Tylenchoidea - drug effects
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Summary:A novel series of chiral fluorinated pyrazole carboxamides derivatives were designed and synthesized. The nematocidal activity was determined. Some of them exhibited good activity. Structure–activity relationship was carried out by docking. [Display omitted] 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.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2016.06.004