N -Cyano sulfilimine functional group as a nonclassical amide bond bioisostere in the design of a potent analogue to anthranilic diamide insecticide

To explore the potential of the -cyano sulfilimine group as an amide bond isostere, a derivative of the blockbuster anthranilic diamide, chlorantramiliprole, was synthesized and evaluated with regard to its physicochemical properties, permeability, and biological activity. Given the combination of -...

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Bibliographic Details
Published in:RSC advances 2023-01, Vol.13 (3), p.2004-2009
Main Authors: Kang, On-Yu, Kim, Eunsil, Lee, Won Hyung, Ryu, Do Hyun, Lim, Hwan Jung, Park, Seong Jun
Format: Article
Language:English
Subjects:
Biological activity
Biological properties
Chemistry
Functional groups
Hydrogen bonds
Permeability
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Summary:To explore the potential of the -cyano sulfilimine group as an amide bond isostere, a derivative of the blockbuster anthranilic diamide, chlorantramiliprole, was synthesized and evaluated with regard to its physicochemical properties, permeability, and biological activity. Given the combination of -cyano sulfilimine chlorantraniliprole 1 and its strong hydrogen bond acceptor character, high permeability, and excellent insecticidal activity, the -cyano sulfilimine functional group could be considered as an amide bond isostere.
ISSN:2046-2069
2046-2069
DOI:10.1039/d2ra06988a