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Steric and electronic effects on the (1)H hyperpolarisation of substituted pyridazines by signal amplification by reversible exchange
Utility of the pyridazine motif is growing in popularity as pharmaceutical and agrochemical agents. The detection and structural characterisation of such materials is therefore imperative for the successful development of new products. Signal amplification by reversible exchange (SABRE) offers a rou...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8650576/ https://www.ncbi.nlm.nih.gov/pubmed/33729592 http://dx.doi.org/10.1002/mrc.5152 |
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author | Rayner, Peter J. Burns, Michael J. Fear, Elizabeth J. Duckett, Simon B. |
author_facet | Rayner, Peter J. Burns, Michael J. Fear, Elizabeth J. Duckett, Simon B. |
author_sort | Rayner, Peter J. |
collection | PubMed |
description | Utility of the pyridazine motif is growing in popularity as pharmaceutical and agrochemical agents. The detection and structural characterisation of such materials is therefore imperative for the successful development of new products. Signal amplification by reversible exchange (SABRE) offers a route to dramatically improve the sensitivity of magnetic resonance methods, and we apply it here to the rapid and cost‐effective hyperpolarisation of substituted pyridazines. The 33 substrates investigated cover a range of steric and electronic properties and their capacity to perform highly effective SABRE is assessed. We find the method to be tolerant to a broad range of electron donating and withdrawing groups; however, good sensitivity is evident when steric bulk is added to the 3‐ and 6‐positions of the pyridazine ring. We optimise the method by reference to a disubstituted ester that yields signal gains of >9000‐fold at 9.4 T (>28% spin polarisation). |
format | Online Article Text |
id | pubmed-8650576 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-86505762021-12-20 Steric and electronic effects on the (1)H hyperpolarisation of substituted pyridazines by signal amplification by reversible exchange Rayner, Peter J. Burns, Michael J. Fear, Elizabeth J. Duckett, Simon B. Magn Reson Chem Special Issue Research Articles Utility of the pyridazine motif is growing in popularity as pharmaceutical and agrochemical agents. The detection and structural characterisation of such materials is therefore imperative for the successful development of new products. Signal amplification by reversible exchange (SABRE) offers a route to dramatically improve the sensitivity of magnetic resonance methods, and we apply it here to the rapid and cost‐effective hyperpolarisation of substituted pyridazines. The 33 substrates investigated cover a range of steric and electronic properties and their capacity to perform highly effective SABRE is assessed. We find the method to be tolerant to a broad range of electron donating and withdrawing groups; however, good sensitivity is evident when steric bulk is added to the 3‐ and 6‐positions of the pyridazine ring. We optimise the method by reference to a disubstituted ester that yields signal gains of >9000‐fold at 9.4 T (>28% spin polarisation). John Wiley and Sons Inc. 2021-04-05 2021-12 /pmc/articles/PMC8650576/ /pubmed/33729592 http://dx.doi.org/10.1002/mrc.5152 Text en © 2021 The Authors. Magnetic Resonance in Chemistry published by John Wiley & Sons Ltd. https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Special Issue Research Articles Rayner, Peter J. Burns, Michael J. Fear, Elizabeth J. Duckett, Simon B. Steric and electronic effects on the (1)H hyperpolarisation of substituted pyridazines by signal amplification by reversible exchange |
title | Steric and electronic effects on the (1)H hyperpolarisation of substituted pyridazines by signal amplification by reversible exchange |
title_full | Steric and electronic effects on the (1)H hyperpolarisation of substituted pyridazines by signal amplification by reversible exchange |
title_fullStr | Steric and electronic effects on the (1)H hyperpolarisation of substituted pyridazines by signal amplification by reversible exchange |
title_full_unstemmed | Steric and electronic effects on the (1)H hyperpolarisation of substituted pyridazines by signal amplification by reversible exchange |
title_short | Steric and electronic effects on the (1)H hyperpolarisation of substituted pyridazines by signal amplification by reversible exchange |
title_sort | steric and electronic effects on the (1)h hyperpolarisation of substituted pyridazines by signal amplification by reversible exchange |
topic | Special Issue Research Articles |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8650576/ https://www.ncbi.nlm.nih.gov/pubmed/33729592 http://dx.doi.org/10.1002/mrc.5152 |
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