Synthesis and carbonic anhydrase I, II, VII, and IX inhibition studies with a series of benzo[d]thiazole-5- and 6-sulfonamides
A series of benzo[d]thiazole-5- and 6-sulfonamides has been synthesized and investigated for the inhibition of several human (h) carbonic anhydrase (CA, EC 4.2.1.1) isoforms, using ethoxzolamide (EZA) as lead molecule. 2-Amino-substituted, 2-acylamino- and halogenated (bromo-and iodo-derivatives at...
| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
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Taylor & Francis Group
2017-01-01
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| Series: | Journal of Enzyme Inhibition and Medicinal Chemistry |
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| Online Access: | http://dx.doi.org/10.1080/14756366.2017.1356295 |
| _version_ | 1819030717951115264 |
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| author | Morteza Abdoli Andrea Angeli Murat Bozdag Fabrizio Carta Ali Kakanejadifard Hamid Saeidian Claudiu T. Supuran |
| author_facet | Morteza Abdoli Andrea Angeli Murat Bozdag Fabrizio Carta Ali Kakanejadifard Hamid Saeidian Claudiu T. Supuran |
| author_sort | Morteza Abdoli |
| collection | DOAJ |
| description | A series of benzo[d]thiazole-5- and 6-sulfonamides has been synthesized and investigated for the inhibition of several human (h) carbonic anhydrase (CA, EC 4.2.1.1) isoforms, using ethoxzolamide (EZA) as lead molecule. 2-Amino-substituted, 2-acylamino- and halogenated (bromo-and iodo-derivatives at the heterocyclic ring) compounds led to several interesting inhibitors against the cytosolic hCA I, II and VII, as well as the transmembrane, tumor-associated hCA IX isoforms. Several subnanomolar/low nanomolar, isoform-selective sulfonamide inhibitors targeting hCA II, VII and IX were detected. The sharp structure–activity relationship for CA inhibition with this small series of derivatives, with important changes of activity observed even after minor changes in the scaffold or at the 2-amino moiety, make this class of scarcely investigated sulfonamides of particular interest for further investigations. |
| first_indexed | 2024-12-21T06:34:36Z |
| format | Article |
| id | doaj.art-014c76875d1d42269bf4de758fa8e93d |
| institution | Directory Open Access Journal |
| issn | 1475-6366 1475-6374 |
| language | English |
| last_indexed | 2024-12-21T06:34:36Z |
| publishDate | 2017-01-01 |
| publisher | Taylor & Francis Group |
| record_format | Article |
| series | Journal of Enzyme Inhibition and Medicinal Chemistry |
| spelling | doaj.art-014c76875d1d42269bf4de758fa8e93d2022-12-21T19:12:55ZengTaylor & Francis GroupJournal of Enzyme Inhibition and Medicinal Chemistry1475-63661475-63742017-01-013211071107810.1080/14756366.2017.13562951356295Synthesis and carbonic anhydrase I, II, VII, and IX inhibition studies with a series of benzo[d]thiazole-5- and 6-sulfonamidesMorteza Abdoli0Andrea Angeli1Murat Bozdag2Fabrizio Carta3Ali Kakanejadifard4Hamid Saeidian5Claudiu T. Supuran6Lorestan UniversityUniversità degli Studi di FirenzeUniversità degli Studi di FirenzeUniversità degli Studi di FirenzeLorestan UniversityPayame Noor University (PNU)Università degli Studi di FirenzeA series of benzo[d]thiazole-5- and 6-sulfonamides has been synthesized and investigated for the inhibition of several human (h) carbonic anhydrase (CA, EC 4.2.1.1) isoforms, using ethoxzolamide (EZA) as lead molecule. 2-Amino-substituted, 2-acylamino- and halogenated (bromo-and iodo-derivatives at the heterocyclic ring) compounds led to several interesting inhibitors against the cytosolic hCA I, II and VII, as well as the transmembrane, tumor-associated hCA IX isoforms. Several subnanomolar/low nanomolar, isoform-selective sulfonamide inhibitors targeting hCA II, VII and IX were detected. The sharp structure–activity relationship for CA inhibition with this small series of derivatives, with important changes of activity observed even after minor changes in the scaffold or at the 2-amino moiety, make this class of scarcely investigated sulfonamides of particular interest for further investigations.http://dx.doi.org/10.1080/14756366.2017.1356295Carbonic anhydrasesulfonamideinhibitorbenzo[d]thiazolescaffold |
| spellingShingle | Morteza Abdoli Andrea Angeli Murat Bozdag Fabrizio Carta Ali Kakanejadifard Hamid Saeidian Claudiu T. Supuran Synthesis and carbonic anhydrase I, II, VII, and IX inhibition studies with a series of benzo[d]thiazole-5- and 6-sulfonamides Journal of Enzyme Inhibition and Medicinal Chemistry Carbonic anhydrase sulfonamide inhibitor benzo[d]thiazole scaffold |
| title | Synthesis and carbonic anhydrase I, II, VII, and IX inhibition studies with a series of benzo[d]thiazole-5- and 6-sulfonamides |
| title_full | Synthesis and carbonic anhydrase I, II, VII, and IX inhibition studies with a series of benzo[d]thiazole-5- and 6-sulfonamides |
| title_fullStr | Synthesis and carbonic anhydrase I, II, VII, and IX inhibition studies with a series of benzo[d]thiazole-5- and 6-sulfonamides |
| title_full_unstemmed | Synthesis and carbonic anhydrase I, II, VII, and IX inhibition studies with a series of benzo[d]thiazole-5- and 6-sulfonamides |
| title_short | Synthesis and carbonic anhydrase I, II, VII, and IX inhibition studies with a series of benzo[d]thiazole-5- and 6-sulfonamides |
| title_sort | synthesis and carbonic anhydrase i ii vii and ix inhibition studies with a series of benzo d thiazole 5 and 6 sulfonamides |
| topic | Carbonic anhydrase sulfonamide inhibitor benzo[d]thiazole scaffold |
| url | http://dx.doi.org/10.1080/14756366.2017.1356295 |
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