1,2-Disubstituted Bicyclo[2.1.1]hexanes as Bioisosteres                                          of the ortho-substituted Benzene

Aleksandr  Denisenko; Pavel  Garbuz; Yelyzaveta  Makovetska; Oleh  Shablykin; Dmytro  Lesyk; Galeb  Al-Maali; Rodion  Korzh; Iryna  Sadkova; Pavel Mykhailiuk

doi:10.26434/chemrxiv-2023-78z7p

Biological and Medicinal Chemistry

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1,2-Disubstituted Bicyclo[2.1.1]hexanes as Bioisosteres of the ortho-substituted Benzene

22 August 2023, Version 1

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Abstract

1,2-Disubstitued bicyclo[2.1.1]hexanes have been designed, synthesized, and validated as a new generation of saturated bioisosteres of ortho-substituted benzenes. Incorporation of the bicyclo[2.1.1]hexane core into the structure of agrochemicals Boskalid (BASF), Bixafen (Bayer CS), and Fluxapyroxad (BASF) gave saturated analogs that exhibited a high antifungal activity.

Keywords

Bicyclo[2.1.1]hexanes

bicyclo[1.1.1]pentanes

bioisosteres

ortho-substituted benzenes

conformational restriction

Supplementary materials

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Description

Experimental procedures, copies of NMR spectra.

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Aug 22, 2023 Version 1

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The content is available under CC BY NC ND 4.0

DOI

10.26434/chemrxiv-2023-78z7p

Funding

European Research Council

101000893

Author’s competing interest statement

Authors of this work are employees of a chemical supplier Enamine.

Ethics

The author(s) declare that they have sought and gained approval from the relevant ethics committee/IRB for this research and its publication.