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Synthesis of a new series of 3-functionalised-1-phenyl-1,2,3-triazole sulfamoylbenzamides as carbonic anhydrase I, II, IV and IX inhibitors
The synthesis of a novel series of 3-functionalised benzenesulfonamides incorporating phenyl-1,2,3-triazole with an amide linker was achieved by using the “click-tail” approach. The new compounds, including the intermediates, were assayed as inhibitors of human carbonic anhydrase (CA, EC 4.2.1.1) is...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Taylor & Francis
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6598542/ https://www.ncbi.nlm.nih.gov/pubmed/31237458 http://dx.doi.org/10.1080/14756366.2019.1629432 |
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author | Swain, Baijayantimala Angeli, Andrea Angapelly, Srinivas Thacker, Pavitra S. Singh, Priti Supuran, Claudiu T. Arifuddin, Mohammed |
author_facet | Swain, Baijayantimala Angeli, Andrea Angapelly, Srinivas Thacker, Pavitra S. Singh, Priti Supuran, Claudiu T. Arifuddin, Mohammed |
author_sort | Swain, Baijayantimala |
collection | PubMed |
description | The synthesis of a novel series of 3-functionalised benzenesulfonamides incorporating phenyl-1,2,3-triazole with an amide linker was achieved by using the “click-tail” approach. The new compounds, including the intermediates, were assayed as inhibitors of human carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA I and II (cytosolic isoforms) and also for hCA IV and IX (transmembrane isoforms) taking acetazolamide as standard drug. Most of these compounds exhibited excellent activity against all these isoforms. hCA I was inhibited with K(i)s in the range of 50.8–966.8 nM, while the glaucoma associated hCA II was inhibited with K(i)s in the range of 6.5–760.0 nM. Isoform hCA IV was inhibited with K(i)s in the range of 65.3–957.5 nM, whereas the tumor associated hypoxia induced hCA IX was inhibited with K(i)s in the range of 30.8–815.9 nM. The structure activity relationship study for the 3-functionalised-1-phenyl-1,2,3-triazole sulfamoylbenzamides against these isoforms was also inferred from the results. |
format | Online Article Text |
id | pubmed-6598542 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | Taylor & Francis |
record_format | MEDLINE/PubMed |
spelling | pubmed-65985422019-07-03 Synthesis of a new series of 3-functionalised-1-phenyl-1,2,3-triazole sulfamoylbenzamides as carbonic anhydrase I, II, IV and IX inhibitors Swain, Baijayantimala Angeli, Andrea Angapelly, Srinivas Thacker, Pavitra S. Singh, Priti Supuran, Claudiu T. Arifuddin, Mohammed J Enzyme Inhib Med Chem Research Paper The synthesis of a novel series of 3-functionalised benzenesulfonamides incorporating phenyl-1,2,3-triazole with an amide linker was achieved by using the “click-tail” approach. The new compounds, including the intermediates, were assayed as inhibitors of human carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA I and II (cytosolic isoforms) and also for hCA IV and IX (transmembrane isoforms) taking acetazolamide as standard drug. Most of these compounds exhibited excellent activity against all these isoforms. hCA I was inhibited with K(i)s in the range of 50.8–966.8 nM, while the glaucoma associated hCA II was inhibited with K(i)s in the range of 6.5–760.0 nM. Isoform hCA IV was inhibited with K(i)s in the range of 65.3–957.5 nM, whereas the tumor associated hypoxia induced hCA IX was inhibited with K(i)s in the range of 30.8–815.9 nM. The structure activity relationship study for the 3-functionalised-1-phenyl-1,2,3-triazole sulfamoylbenzamides against these isoforms was also inferred from the results. Taylor & Francis 2019-06-25 /pmc/articles/PMC6598542/ /pubmed/31237458 http://dx.doi.org/10.1080/14756366.2019.1629432 Text en © 2019 The Author(s). Published by Informa UK Limited, trading as Taylor & Francis Group. http://creativecommons.org/licenses/by/4.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Research Paper Swain, Baijayantimala Angeli, Andrea Angapelly, Srinivas Thacker, Pavitra S. Singh, Priti Supuran, Claudiu T. Arifuddin, Mohammed Synthesis of a new series of 3-functionalised-1-phenyl-1,2,3-triazole sulfamoylbenzamides as carbonic anhydrase I, II, IV and IX inhibitors |
title | Synthesis of a new series of 3-functionalised-1-phenyl-1,2,3-triazole sulfamoylbenzamides as carbonic anhydrase I, II, IV and IX inhibitors |
title_full | Synthesis of a new series of 3-functionalised-1-phenyl-1,2,3-triazole sulfamoylbenzamides as carbonic anhydrase I, II, IV and IX inhibitors |
title_fullStr | Synthesis of a new series of 3-functionalised-1-phenyl-1,2,3-triazole sulfamoylbenzamides as carbonic anhydrase I, II, IV and IX inhibitors |
title_full_unstemmed | Synthesis of a new series of 3-functionalised-1-phenyl-1,2,3-triazole sulfamoylbenzamides as carbonic anhydrase I, II, IV and IX inhibitors |
title_short | Synthesis of a new series of 3-functionalised-1-phenyl-1,2,3-triazole sulfamoylbenzamides as carbonic anhydrase I, II, IV and IX inhibitors |
title_sort | synthesis of a new series of 3-functionalised-1-phenyl-1,2,3-triazole sulfamoylbenzamides as carbonic anhydrase i, ii, iv and ix inhibitors |
topic | Research Paper |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6598542/ https://www.ncbi.nlm.nih.gov/pubmed/31237458 http://dx.doi.org/10.1080/14756366.2019.1629432 |
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