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Iodine/Oxone® oxidative system for the synthesis of selenylindoles bearing a benzenesulfonamide moiety as carbonic anhydrase I, II, IX, and XII inhibitors.
- Source :
-
Organic & biomolecular chemistry [Org Biomol Chem] 2024 Aug 14; Vol. 22 (32), pp. 6532-6542. Date of Electronic Publication: 2024 Aug 14. - Publication Year :
- 2024
-
Abstract
- A wide range of 3-selenylindoles were synthesized via an eco-friendly approach that uses Oxone® as the oxidant in the presence of a catalytic amount of iodine. This mild and economical protocol showed broad functional group tolerance and operational simplicity. A series of novel selenylindoles bearing a benzenesulfonamide moiety were also synthesized and evaluated as carbonic anhydrase inhibitors of the human (h) isoforms hCa I, II, IX, and XII, which are involved in pathologies such as glaucoma and cancer. Several derivatives showed excellent inhibitory activity towards these isoforms in the nanomolar range, lower than that shown by acetazolamide.
- Subjects :
- Humans
Organoselenium Compounds chemistry
Organoselenium Compounds pharmacology
Organoselenium Compounds chemical synthesis
Structure-Activity Relationship
Molecular Structure
Carbonic Anhydrase Inhibitors chemistry
Carbonic Anhydrase Inhibitors pharmacology
Carbonic Anhydrase Inhibitors chemical synthesis
Sulfonamides chemistry
Sulfonamides pharmacology
Sulfonamides chemical synthesis
Carbonic Anhydrases metabolism
Benzenesulfonamides
Indoles chemistry
Indoles pharmacology
Indoles chemical synthesis
Oxidation-Reduction
Iodine chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1477-0539
- Volume :
- 22
- Issue :
- 32
- Database :
- MEDLINE
- Journal :
- Organic & biomolecular chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 39072494
- Full Text :
- https://doi.org/10.1039/d4ob00826j