1,2-Disubstituted bicyclo[2.1.1]hexanes as saturated bioisosteres of ortho-substituted benzene

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

doi:10.1039/D3SC05121H

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1,2-Disubstituted bicyclo[2.1.1]hexanes as saturated bioisosteres of ortho-substituted benzene†

Aleksandr Denisenko,^a Pavel Garbuz,^a Yelyzaveta Makovetska,^a Oleh Shablykin,^ab Dmytro Lesyk,^c Galeb Al-Maali,^ad Rodion Korzh,^a Iryna V. Sadkova^a and Pavel K. Mykhailiuk

*^a

Author affiliations

* Corresponding authors

^a Enamine Ltd, Winston Churchill st. 78, 02094 Kyiv, Ukraine
E-mail: Pavel.Mykhailiuk@gmail.com
Web: www.mykhailiukchem.org

^b V. P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, 02094 Kyiv, Ukraine

^c Bienta, Winston Churchill st. 78, 02094 Kyiv, Ukraine

^d Institute of Botany of the National Academy of Sciences of Ukraine, 02094 Kyiv, Ukraine

Abstract

Bicyclo[2.1.1]hexanes have been synthesized, characterized, and biologically validated as saturated bioisosteres of the ortho-substituted benzene ring. The incorporation of the 1,2-disubstituted bicyclo[2.1.1]hexane core into the structure of fungicides boscalid (BASF), bixafen (Bayer CS), and fluxapyroxad (BASF) gave saturated patent-free analogs with high antifungal activity.

This article is part of the themed collection: 2023 Chemical Science Covers

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DOI: https://doi.org/10.1039/D3SC05121H
Article type: Edge Article
Submitted: 28 Sep 2023
Accepted: 25 Oct 2023
First published: 27 Oct 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry

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Chem. Sci., 2023,14, 14092-14099

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1,2-Disubstituted bicyclo[2.1.1]hexanes as saturated bioisosteres of ortho-substituted benzene

A. Denisenko, P. Garbuz, Y. Makovetska, O. Shablykin, D. Lesyk, G. Al-Maali, R. Korzh, I. V. Sadkova and P. K. Mykhailiuk, Chem. Sci., 2023, 14, 14092 DOI: 10.1039/D3SC05121H

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1,2-Disubstituted bicyclo[2.1.1]hexanes as saturated bioisosteres of ortho-substituted benzene†

Abstract

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1,2-Disubstituted bicyclo[2.1.1]hexanes as saturated bioisosteres of ortho-substituted benzene

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