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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...

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Autores principales: Swain, Baijayantimala, Angeli, Andrea, Angapelly, Srinivas, Thacker, Pavitra S., Singh, Priti, Supuran, Claudiu T., Arifuddin, Mohammed
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Taylor & Francis 2019
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.
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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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