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Conquering the Synthesis and Functionalization of Bicyclo[1.1.1]pentanes
[Image: see text] Bicyclo[1.1.1]pentanes (BCPs) have become established as attractive bioisosteres for para-substituted benzene rings in drug design. Conferring various beneficial properties compared with their aromatic “parents,” BCPs featuring a wide array of bridgehead substituents can now be acc...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2023
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10301682/ https://www.ncbi.nlm.nih.gov/pubmed/37388694 http://dx.doi.org/10.1021/jacsau.3c00014 |
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author | Shire, Bethany R. Anderson, Edward A. |
author_facet | Shire, Bethany R. Anderson, Edward A. |
author_sort | Shire, Bethany R. |
collection | PubMed |
description | [Image: see text] Bicyclo[1.1.1]pentanes (BCPs) have become established as attractive bioisosteres for para-substituted benzene rings in drug design. Conferring various beneficial properties compared with their aromatic “parents,” BCPs featuring a wide array of bridgehead substituents can now be accessed by an equivalent variety of methods. In this perspective, we discuss the evolution of this field and focus on the most enabling and general methods for BCPs synthesis, considering both scope and limitation. Recent breakthroughs on the synthesis of bridge-substituted BCPs are described, as well as methodologies for postsynthesis functionalization. We further explore new challenges and directions for the field, such as the emergence of other rigid small ring hydrocarbons and heterocycles possessing unique substituent exit vectors. |
format | Online Article Text |
id | pubmed-10301682 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-103016822023-06-29 Conquering the Synthesis and Functionalization of Bicyclo[1.1.1]pentanes Shire, Bethany R. Anderson, Edward A. JACS Au [Image: see text] Bicyclo[1.1.1]pentanes (BCPs) have become established as attractive bioisosteres for para-substituted benzene rings in drug design. Conferring various beneficial properties compared with their aromatic “parents,” BCPs featuring a wide array of bridgehead substituents can now be accessed by an equivalent variety of methods. In this perspective, we discuss the evolution of this field and focus on the most enabling and general methods for BCPs synthesis, considering both scope and limitation. Recent breakthroughs on the synthesis of bridge-substituted BCPs are described, as well as methodologies for postsynthesis functionalization. We further explore new challenges and directions for the field, such as the emergence of other rigid small ring hydrocarbons and heterocycles possessing unique substituent exit vectors. American Chemical Society 2023-05-16 /pmc/articles/PMC10301682/ /pubmed/37388694 http://dx.doi.org/10.1021/jacsau.3c00014 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Shire, Bethany R. Anderson, Edward A. Conquering the Synthesis and Functionalization of Bicyclo[1.1.1]pentanes |
title | Conquering the Synthesis and Functionalization of
Bicyclo[1.1.1]pentanes |
title_full | Conquering the Synthesis and Functionalization of
Bicyclo[1.1.1]pentanes |
title_fullStr | Conquering the Synthesis and Functionalization of
Bicyclo[1.1.1]pentanes |
title_full_unstemmed | Conquering the Synthesis and Functionalization of
Bicyclo[1.1.1]pentanes |
title_short | Conquering the Synthesis and Functionalization of
Bicyclo[1.1.1]pentanes |
title_sort | conquering the synthesis and functionalization of
bicyclo[1.1.1]pentanes |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10301682/ https://www.ncbi.nlm.nih.gov/pubmed/37388694 http://dx.doi.org/10.1021/jacsau.3c00014 |
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