Novel sulphonamides incorporating triazene moieties show powerful carbonic anhydrase I and II inhibitory properties
A series of compounds incorporating 3-(3-(2/3/4-substituted phenyl)triaz-1-en-1-yl) benzenesulfonamide moieties were synthesised and their chemical structure was confirmed by physico-chemical methods. Carbonic anhydrase (CA, EC 4.2.1.1) inhibitory effects of the compounds were evaluated against huma...
| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
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Taylor & Francis Group
2020-01-01
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| Series: | Journal of Enzyme Inhibition and Medicinal Chemistry |
| Subjects: | |
| Online Access: | http://dx.doi.org/10.1080/14756366.2019.1700240 |
| _version_ | 1818972864651460608 |
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| author | Sinan Bilginer Baris Gonder Halise Inci Gul Ruya Kaya Ilhami Gulcin Baris Anil Claudiu T. Supuran |
| author_facet | Sinan Bilginer Baris Gonder Halise Inci Gul Ruya Kaya Ilhami Gulcin Baris Anil Claudiu T. Supuran |
| author_sort | Sinan Bilginer |
| collection | DOAJ |
| description | A series of compounds incorporating 3-(3-(2/3/4-substituted phenyl)triaz-1-en-1-yl) benzenesulfonamide moieties were synthesised and their chemical structure was confirmed by physico-chemical methods. Carbonic anhydrase (CA, EC 4.2.1.1) inhibitory effects of the compounds were evaluated against human isoforms hCA I and II. KI values of these sulphonamides were in the range of 21 ± 4–72 ± 2 nM towards hCA I and in the range of 16 ± 6–40 ± 2 nM against hCA II. The 4-fluoro substituted derivative might be considered as an interesting lead due to its effective inhibitory action against both hCA I and hCA II (KIs of 21 nM), a profile rarely seen among other sulphonamide CA inhibitors, making it of interest in systems where the activity of the two cytosolic isoforms is dysregulated. |
| first_indexed | 2024-12-20T15:15:03Z |
| format | Article |
| id | doaj.art-023f570a320b4b30b2f0bafdf130d342 |
| institution | Directory Open Access Journal |
| issn | 1475-6366 1475-6374 |
| language | English |
| last_indexed | 2024-12-20T15:15:03Z |
| publishDate | 2020-01-01 |
| publisher | Taylor & Francis Group |
| record_format | Article |
| series | Journal of Enzyme Inhibition and Medicinal Chemistry |
| spelling | doaj.art-023f570a320b4b30b2f0bafdf130d3422022-12-21T19:36:10ZengTaylor & Francis GroupJournal of Enzyme Inhibition and Medicinal Chemistry1475-63661475-63742020-01-0135132532910.1080/14756366.2019.17002401700240Novel sulphonamides incorporating triazene moieties show powerful carbonic anhydrase I and II inhibitory propertiesSinan Bilginer0Baris Gonder1Halise Inci Gul2Ruya Kaya3Ilhami Gulcin4Baris Anil5Claudiu T. Supuran6Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ataturk UniversityDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Ataturk UniversityDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Ataturk UniversityDepartment of Chemistry, Faculty of Science, Ataturk UniversityDepartment of Chemistry, Faculty of Science, Ataturk UniversityDepartment of Chemistry, Faculty of Science, Ataturk UniversityNeurofarba Department, University FirenzeA series of compounds incorporating 3-(3-(2/3/4-substituted phenyl)triaz-1-en-1-yl) benzenesulfonamide moieties were synthesised and their chemical structure was confirmed by physico-chemical methods. Carbonic anhydrase (CA, EC 4.2.1.1) inhibitory effects of the compounds were evaluated against human isoforms hCA I and II. KI values of these sulphonamides were in the range of 21 ± 4–72 ± 2 nM towards hCA I and in the range of 16 ± 6–40 ± 2 nM against hCA II. The 4-fluoro substituted derivative might be considered as an interesting lead due to its effective inhibitory action against both hCA I and hCA II (KIs of 21 nM), a profile rarely seen among other sulphonamide CA inhibitors, making it of interest in systems where the activity of the two cytosolic isoforms is dysregulated.http://dx.doi.org/10.1080/14756366.2019.1700240carbonic anhydrasediazonium saltinhibitorsmetanilamidesulphonamidetriazene |
| spellingShingle | Sinan Bilginer Baris Gonder Halise Inci Gul Ruya Kaya Ilhami Gulcin Baris Anil Claudiu T. Supuran Novel sulphonamides incorporating triazene moieties show powerful carbonic anhydrase I and II inhibitory properties Journal of Enzyme Inhibition and Medicinal Chemistry carbonic anhydrase diazonium salt inhibitors metanilamide sulphonamide triazene |
| title | Novel sulphonamides incorporating triazene moieties show powerful carbonic anhydrase I and II inhibitory properties |
| title_full | Novel sulphonamides incorporating triazene moieties show powerful carbonic anhydrase I and II inhibitory properties |
| title_fullStr | Novel sulphonamides incorporating triazene moieties show powerful carbonic anhydrase I and II inhibitory properties |
| title_full_unstemmed | Novel sulphonamides incorporating triazene moieties show powerful carbonic anhydrase I and II inhibitory properties |
| title_short | Novel sulphonamides incorporating triazene moieties show powerful carbonic anhydrase I and II inhibitory properties |
| title_sort | novel sulphonamides incorporating triazene moieties show powerful carbonic anhydrase i and ii inhibitory properties |
| topic | carbonic anhydrase diazonium salt inhibitors metanilamide sulphonamide triazene |
| url | http://dx.doi.org/10.1080/14756366.2019.1700240 |
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