4-Cyanamidobenzenesulfonamide derivatives: a novel class of human and bacterial carbonic anhydrase inhibitors
A one-pot two-step protocol was developed for the synthesis of a series of novel 4-cyanamidobenzenesulfonamides from easily accessible methyl (4-sulfamoylphenyl)-carbamimidothioate. The new sulphonamides were investigated as inhibitors of the enzyme carbonic anhydrase (CA, EC 4.2.1.1), the human (h)...
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| Format: | Article |
| Language: | English |
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Taylor & Francis Group
2023-12-01
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| Series: | Journal of Enzyme Inhibition and Medicinal Chemistry |
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| Online Access: | https://www.tandfonline.com/doi/10.1080/14756366.2022.2138367 |
| _version_ | 1827123366148964352 |
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| author | Morteza Abdoli Alessandro Bonardi Claudiu T. Supuran Raivis Žalubovskis |
| author_facet | Morteza Abdoli Alessandro Bonardi Claudiu T. Supuran Raivis Žalubovskis |
| author_sort | Morteza Abdoli |
| collection | DOAJ |
| description | A one-pot two-step protocol was developed for the synthesis of a series of novel 4-cyanamidobenzenesulfonamides from easily accessible methyl (4-sulfamoylphenyl)-carbamimidothioate. The new sulphonamides were investigated as inhibitors of the enzyme carbonic anhydrase (CA, EC 4.2.1.1), the human (h) cytosolic isoforms hCA I, II, VII, and XIII, as well as three bacterial enzymes belonging to the β-CA class, MscCA from Mammaliicoccus (Staphylococcus) sciuri and StCA1 and StCA2, from Salmonella enterica (serovar Typhimurium). The human isoforms were generally effectively inhibited by these compounds, with a clear structure-activity relationship privileging long aliphatic chains (C6, C7 and C18) as substituents at the cyanamide functionality. The bacterial CAs were also inhibited by these compounds, but not as effective as the hCAs. The most sensitive enzyme to these inhibitors was StCA1 (KIs of 50.7 − 91.1 nM) whereas SscCA was inhibited in the micromolar range (KIs of 0.86–9.59 µM). |
| first_indexed | 2024-03-09T02:03:07Z |
| format | Article |
| id | doaj.art-b78f5378e4f54145a14a8b22ba1dd3de |
| institution | Directory Open Access Journal |
| issn | 1475-6366 1475-6374 |
| language | English |
| last_indexed | 2025-03-20T14:23:47Z |
| publishDate | 2023-12-01 |
| publisher | Taylor & Francis Group |
| record_format | Article |
| series | Journal of Enzyme Inhibition and Medicinal Chemistry |
| spelling | doaj.art-b78f5378e4f54145a14a8b22ba1dd3de2024-09-09T17:23:20ZengTaylor & Francis GroupJournal of Enzyme Inhibition and Medicinal Chemistry1475-63661475-63742023-12-0138115616510.1080/14756366.2022.21383674-Cyanamidobenzenesulfonamide derivatives: a novel class of human and bacterial carbonic anhydrase inhibitorsMorteza Abdoli0Alessandro Bonardi1Claudiu T. Supuran2Raivis Žalubovskis3Faculty of Materials Science and Applied Chemistry, Institute of Technology of Organic Chemistry, Riga Technical University, Riga, LatviaNeurofarba Department, Università degli Studi di Firenze, Florence, ItalyNeurofarba Department, Università degli Studi di Firenze, Florence, ItalyFaculty of Materials Science and Applied Chemistry, Institute of Technology of Organic Chemistry, Riga Technical University, Riga, LatviaA one-pot two-step protocol was developed for the synthesis of a series of novel 4-cyanamidobenzenesulfonamides from easily accessible methyl (4-sulfamoylphenyl)-carbamimidothioate. The new sulphonamides were investigated as inhibitors of the enzyme carbonic anhydrase (CA, EC 4.2.1.1), the human (h) cytosolic isoforms hCA I, II, VII, and XIII, as well as three bacterial enzymes belonging to the β-CA class, MscCA from Mammaliicoccus (Staphylococcus) sciuri and StCA1 and StCA2, from Salmonella enterica (serovar Typhimurium). The human isoforms were generally effectively inhibited by these compounds, with a clear structure-activity relationship privileging long aliphatic chains (C6, C7 and C18) as substituents at the cyanamide functionality. The bacterial CAs were also inhibited by these compounds, but not as effective as the hCAs. The most sensitive enzyme to these inhibitors was StCA1 (KIs of 50.7 − 91.1 nM) whereas SscCA was inhibited in the micromolar range (KIs of 0.86–9.59 µM).https://www.tandfonline.com/doi/10.1080/14756366.2022.2138367Carbonic anhydrasecyanamidessulphonamidesMammaliicoccus (Staphylococcus) sciuriSalmonella enterica (serovar Typhimurium) |
| spellingShingle | Morteza Abdoli Alessandro Bonardi Claudiu T. Supuran Raivis Žalubovskis 4-Cyanamidobenzenesulfonamide derivatives: a novel class of human and bacterial carbonic anhydrase inhibitors Journal of Enzyme Inhibition and Medicinal Chemistry Carbonic anhydrase cyanamides sulphonamides Mammaliicoccus (Staphylococcus) sciuri Salmonella enterica (serovar Typhimurium) |
| title | 4-Cyanamidobenzenesulfonamide derivatives: a novel class of human and bacterial carbonic anhydrase inhibitors |
| title_full | 4-Cyanamidobenzenesulfonamide derivatives: a novel class of human and bacterial carbonic anhydrase inhibitors |
| title_fullStr | 4-Cyanamidobenzenesulfonamide derivatives: a novel class of human and bacterial carbonic anhydrase inhibitors |
| title_full_unstemmed | 4-Cyanamidobenzenesulfonamide derivatives: a novel class of human and bacterial carbonic anhydrase inhibitors |
| title_short | 4-Cyanamidobenzenesulfonamide derivatives: a novel class of human and bacterial carbonic anhydrase inhibitors |
| title_sort | 4 cyanamidobenzenesulfonamide derivatives a novel class of human and bacterial carbonic anhydrase inhibitors |
| topic | Carbonic anhydrase cyanamides sulphonamides Mammaliicoccus (Staphylococcus) sciuri Salmonella enterica (serovar Typhimurium) |
| url | https://www.tandfonline.com/doi/10.1080/14756366.2022.2138367 |
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