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A Scaffold‐Diversity Synthesis of Biologically Intriguing Cyclic Sulfonamides
A “branching–folding” synthetic strategy that affords a range of diverse cyclic benzo‐sulfonamide scaffolds is presented. Whereas different annulation reactions on common ketimine substrates build the branching phase of the scaffold synthesis, a common hydrogenative ring‐expansion method, facilitate...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6916640/ https://www.ncbi.nlm.nih.gov/pubmed/31518018 http://dx.doi.org/10.1002/chem.201904175 |
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author | Zimmermann, Stefan Akbarzadeh, Mohammad Otte, Felix Strohmann, Carsten Sankar, Muthukumar Gomathi Ziegler, Slava Pahl, Axel Sievers, Sonja Kumar, Kamal |
author_facet | Zimmermann, Stefan Akbarzadeh, Mohammad Otte, Felix Strohmann, Carsten Sankar, Muthukumar Gomathi Ziegler, Slava Pahl, Axel Sievers, Sonja Kumar, Kamal |
author_sort | Zimmermann, Stefan |
collection | PubMed |
description | A “branching–folding” synthetic strategy that affords a range of diverse cyclic benzo‐sulfonamide scaffolds is presented. Whereas different annulation reactions on common ketimine substrates build the branching phase of the scaffold synthesis, a common hydrogenative ring‐expansion method, facilitated by an increase of the ring‐strain during the branching phase, led to sulfonamides bearing medium‐sized rings in a folding pathway. Cell painting assay was successfully employed to identify tubulin targeting sulfonamides as novel mitotic inhibitors. |
format | Online Article Text |
id | pubmed-6916640 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-69166402019-12-23 A Scaffold‐Diversity Synthesis of Biologically Intriguing Cyclic Sulfonamides Zimmermann, Stefan Akbarzadeh, Mohammad Otte, Felix Strohmann, Carsten Sankar, Muthukumar Gomathi Ziegler, Slava Pahl, Axel Sievers, Sonja Kumar, Kamal Chemistry Communications A “branching–folding” synthetic strategy that affords a range of diverse cyclic benzo‐sulfonamide scaffolds is presented. Whereas different annulation reactions on common ketimine substrates build the branching phase of the scaffold synthesis, a common hydrogenative ring‐expansion method, facilitated by an increase of the ring‐strain during the branching phase, led to sulfonamides bearing medium‐sized rings in a folding pathway. Cell painting assay was successfully employed to identify tubulin targeting sulfonamides as novel mitotic inhibitors. John Wiley and Sons Inc. 2019-11-07 2019-12-05 /pmc/articles/PMC6916640/ /pubmed/31518018 http://dx.doi.org/10.1002/chem.201904175 Text en © 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes. |
spellingShingle | Communications Zimmermann, Stefan Akbarzadeh, Mohammad Otte, Felix Strohmann, Carsten Sankar, Muthukumar Gomathi Ziegler, Slava Pahl, Axel Sievers, Sonja Kumar, Kamal A Scaffold‐Diversity Synthesis of Biologically Intriguing Cyclic Sulfonamides |
title | A Scaffold‐Diversity Synthesis of Biologically Intriguing Cyclic Sulfonamides |
title_full | A Scaffold‐Diversity Synthesis of Biologically Intriguing Cyclic Sulfonamides |
title_fullStr | A Scaffold‐Diversity Synthesis of Biologically Intriguing Cyclic Sulfonamides |
title_full_unstemmed | A Scaffold‐Diversity Synthesis of Biologically Intriguing Cyclic Sulfonamides |
title_short | A Scaffold‐Diversity Synthesis of Biologically Intriguing Cyclic Sulfonamides |
title_sort | scaffold‐diversity synthesis of biologically intriguing cyclic sulfonamides |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6916640/ https://www.ncbi.nlm.nih.gov/pubmed/31518018 http://dx.doi.org/10.1002/chem.201904175 |
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