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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...

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Autores principales: Zimmermann, Stefan, Akbarzadeh, Mohammad, Otte, Felix, Strohmann, Carsten, Sankar, Muthukumar Gomathi, Ziegler, Slava, Pahl, Axel, Sievers, Sonja, Kumar, Kamal
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2019
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.
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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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