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Discovery, development, chemical diversity and design of isoxazoline-based insecticides.

Discovery, development, chemical diversity and design of isoxazoline-based insecticides.

Authors :
Gonçalves IL
Machado das Neves G
Porto Kagami L
Eifler-Lima VL
Merlo AA
Source :
Bioorganic & medicinal chemistry [Bioorg Med Chem] 2021 Jan 15; Vol. 30, pp. 115934. Date of Electronic Publication: 2020 Dec 09.
Publication Year :
2021

Abstract

Isoxazoline is a 5-membered heterocycle present in the active compounds of many commercial veterinary anti-ectoparasitic products. The molecular target of isoxazolines is the inhibition of GABA-gated chloride channels in insects. These facts have inspired the use of the isoxazoline scaffold in the design of novel insecticide compounds. The main strategies used for isoxazoline synthesis are either the 1,3-dipolar cycloaddition between a nitrile oxide and an alkene or the reaction between hydroxylamine and an α,β-unsaturated carbonyl compound. This review highlights the utilization of isoxazoline as insecticide: its mode of action, its commercial preparations and its consideration in the design of novel insecticides. Similarity analyses were performed with 235 isoxazoline derivatives in three different cheminformatic approaches - chemical property correlations, similarity network and compound clustering. The cheminformatic methodologies are interesting tools to use in evaluating the similarity between commercial isoxazolines and to clarify the main features explored within their derivatives.<br /> (Copyright © 2020 Elsevier Ltd. All rights reserved.)

Details

Language :
English
ISSN :
1464-3391
Volume :
30
Database :
MEDLINE
Journal :
Bioorganic & medicinal chemistry
Publication Type :
Academic Journal
Accession number :
33360575
Full Text :
https://doi.org/10.1016/j.bmc.2020.115934