2-((1H-Benzo[d]imidazol-2-yl)amino)benzo[d]thiazole-6-sulphonamides: a class of carbonic anhydrase II and VII-selective inhibitors
A small library of substituted cyclic guanidine incorporated benzothiazole-6-sulphonamides was synthesized. All obtained compounds were investigated for their inhibitory activity against the key brain-associated human carbonic anhydrase isoform hCA VII (a promising target for the treatment of neurop...
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| Format: | Article |
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Taylor & Francis Group
2023-12-01
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| Series: | Journal of Enzyme Inhibition and Medicinal Chemistry |
| Subjects: | |
| Online Access: | https://www.tandfonline.com/doi/10.1080/14756366.2023.2174981 |
| _version_ | 1827123363130114048 |
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| author | Morteza Abdoli Claudiu T. Supuran Raivis Žalubovskis |
| author_facet | Morteza Abdoli Claudiu T. Supuran Raivis Žalubovskis |
| author_sort | Morteza Abdoli |
| collection | DOAJ |
| description | A small library of substituted cyclic guanidine incorporated benzothiazole-6-sulphonamides was synthesized. All obtained compounds were investigated for their inhibitory activity against the key brain-associated human carbonic anhydrase isoform hCA VII (a promising target for the treatment of neuropathic pain) and three isoforms expressed in brain and other tissues, hCA I, II, and IV. Sulphaguanidine derivatives 9a–d were inactive on the all investigated isoforms while the primary sulphonamide containing guanidines 6a–c and 7a–c were inactive towards hCA IV but displayed inhibiting properties on hCA I, II, and VII with KIs values in the low nanomolar to micromolar ranges. The results indicated that isoforms hCA II and VII were potently and selectively inhibited by these compounds, whereas the cytosolic hCA I was less sensitive to inhibition. The derivatives reported in this study might be useful for design of more potent and selective inhibitors of hCA II and VII. |
| first_indexed | 2024-03-09T02:03:05Z |
| format | Article |
| id | doaj.art-ac94d438f7864dc59e74771f97c2ed5a |
| institution | Directory Open Access Journal |
| issn | 1475-6366 1475-6374 |
| language | English |
| last_indexed | 2025-03-20T14:23:44Z |
| publishDate | 2023-12-01 |
| publisher | Taylor & Francis Group |
| record_format | Article |
| series | Journal of Enzyme Inhibition and Medicinal Chemistry |
| spelling | doaj.art-ac94d438f7864dc59e74771f97c2ed5a2024-09-09T17:23:18ZengTaylor & Francis GroupJournal of Enzyme Inhibition and Medicinal Chemistry1475-63661475-63742023-12-0138110.1080/14756366.2023.21749812-((1H-Benzo[d]imidazol-2-yl)amino)benzo[d]thiazole-6-sulphonamides: a class of carbonic anhydrase II and VII-selective inhibitorsMorteza Abdoli0Claudiu T. Supuran1Raivis Žalubovskis2Institute of Technology of Organic Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, Riga, LatviaNEUROFARBA Department, Pharmaceutical and Nutraceutical Section, University of Florence, Florence, ItalyInstitute of Technology of Organic Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, Riga, LatviaA small library of substituted cyclic guanidine incorporated benzothiazole-6-sulphonamides was synthesized. All obtained compounds were investigated for their inhibitory activity against the key brain-associated human carbonic anhydrase isoform hCA VII (a promising target for the treatment of neuropathic pain) and three isoforms expressed in brain and other tissues, hCA I, II, and IV. Sulphaguanidine derivatives 9a–d were inactive on the all investigated isoforms while the primary sulphonamide containing guanidines 6a–c and 7a–c were inactive towards hCA IV but displayed inhibiting properties on hCA I, II, and VII with KIs values in the low nanomolar to micromolar ranges. The results indicated that isoforms hCA II and VII were potently and selectively inhibited by these compounds, whereas the cytosolic hCA I was less sensitive to inhibition. The derivatives reported in this study might be useful for design of more potent and selective inhibitors of hCA II and VII.https://www.tandfonline.com/doi/10.1080/14756366.2023.2174981Carbonic anhydrase isozyme VIIneuropathic painsulphonamidesguanidinesinhibitors |
| spellingShingle | Morteza Abdoli Claudiu T. Supuran Raivis Žalubovskis 2-((1H-Benzo[d]imidazol-2-yl)amino)benzo[d]thiazole-6-sulphonamides: a class of carbonic anhydrase II and VII-selective inhibitors Journal of Enzyme Inhibition and Medicinal Chemistry Carbonic anhydrase isozyme VII neuropathic pain sulphonamides guanidines inhibitors |
| title | 2-((1H-Benzo[d]imidazol-2-yl)amino)benzo[d]thiazole-6-sulphonamides: a class of carbonic anhydrase II and VII-selective inhibitors |
| title_full | 2-((1H-Benzo[d]imidazol-2-yl)amino)benzo[d]thiazole-6-sulphonamides: a class of carbonic anhydrase II and VII-selective inhibitors |
| title_fullStr | 2-((1H-Benzo[d]imidazol-2-yl)amino)benzo[d]thiazole-6-sulphonamides: a class of carbonic anhydrase II and VII-selective inhibitors |
| title_full_unstemmed | 2-((1H-Benzo[d]imidazol-2-yl)amino)benzo[d]thiazole-6-sulphonamides: a class of carbonic anhydrase II and VII-selective inhibitors |
| title_short | 2-((1H-Benzo[d]imidazol-2-yl)amino)benzo[d]thiazole-6-sulphonamides: a class of carbonic anhydrase II and VII-selective inhibitors |
| title_sort | 2 1h benzo d imidazol 2 yl amino benzo d thiazole 6 sulphonamides a class of carbonic anhydrase ii and vii selective inhibitors |
| topic | Carbonic anhydrase isozyme VII neuropathic pain sulphonamides guanidines inhibitors |
| url | https://www.tandfonline.com/doi/10.1080/14756366.2023.2174981 |
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