2,5-disubstituted bicyclo[2.1.1]hexanes as rigidified cyclopentane variants

Identification of rigid counterparts for common flexible scaffolds is crucial to the advancement of medicinal chemistry. Here we showcase a new class of building blocks, 2,5-disubstituted bicyclo[2.1.1]hexanes that can act as rigidified cis-, or trans-1,3-disubstituted cyclopentanes, common motifs i...

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Detalles Bibliográficos
Autores principales: Paul, Shashwati, Adelfinsky, Daniel, Salome, Christophe, Fessard, Thomas, Brown, M. Kevin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10395266/
https://www.ncbi.nlm.nih.gov/pubmed/37538817
http://dx.doi.org/10.1039/d3sc02695g
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author Paul, Shashwati
Adelfinsky, Daniel
Salome, Christophe
Fessard, Thomas
Brown, M. Kevin
author_facet Paul, Shashwati
Adelfinsky, Daniel
Salome, Christophe
Fessard, Thomas
Brown, M. Kevin
author_sort Paul, Shashwati
collection PubMed
description Identification of rigid counterparts for common flexible scaffolds is crucial to the advancement of medicinal chemistry. Here we showcase a new class of building blocks, 2,5-disubstituted bicyclo[2.1.1]hexanes that can act as rigidified cis-, or trans-1,3-disubstituted cyclopentanes, common motifs in drugs. The scalable synthesis of these structures was enabled through the use of C–H functionalization logic and cycloaddition reactions.
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spelling pubmed-103952662023-08-03 2,5-disubstituted bicyclo[2.1.1]hexanes as rigidified cyclopentane variants Paul, Shashwati Adelfinsky, Daniel Salome, Christophe Fessard, Thomas Brown, M. Kevin Chem Sci Chemistry Identification of rigid counterparts for common flexible scaffolds is crucial to the advancement of medicinal chemistry. Here we showcase a new class of building blocks, 2,5-disubstituted bicyclo[2.1.1]hexanes that can act as rigidified cis-, or trans-1,3-disubstituted cyclopentanes, common motifs in drugs. The scalable synthesis of these structures was enabled through the use of C–H functionalization logic and cycloaddition reactions. The Royal Society of Chemistry 2023-07-12 /pmc/articles/PMC10395266/ /pubmed/37538817 http://dx.doi.org/10.1039/d3sc02695g Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Paul, Shashwati
Adelfinsky, Daniel
Salome, Christophe
Fessard, Thomas
Brown, M. Kevin
2,5-disubstituted bicyclo[2.1.1]hexanes as rigidified cyclopentane variants
title 2,5-disubstituted bicyclo[2.1.1]hexanes as rigidified cyclopentane variants
title_full 2,5-disubstituted bicyclo[2.1.1]hexanes as rigidified cyclopentane variants
title_fullStr 2,5-disubstituted bicyclo[2.1.1]hexanes as rigidified cyclopentane variants
title_full_unstemmed 2,5-disubstituted bicyclo[2.1.1]hexanes as rigidified cyclopentane variants
title_short 2,5-disubstituted bicyclo[2.1.1]hexanes as rigidified cyclopentane variants
title_sort 2,5-disubstituted bicyclo[2.1.1]hexanes as rigidified cyclopentane variants
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10395266/
https://www.ncbi.nlm.nih.gov/pubmed/37538817
http://dx.doi.org/10.1039/d3sc02695g
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