Abstract
A small series of N-glycosylsulfonamides incorporating the phenol moiety has been prepared by Ferrier sulfonamidoglycosylation of d-glycals. N-Glycosides were tested for the inhibition of four isoforms of carbonic anhydrase. In this study, all compounds showed good inhibitory activity against hCA I and II, with selectivity against the cytosolic hCA II versus the tumor associated isozymes. These results confirm that attaching carbohydrate moieties to CA phenol pharmacophore improves and enhances its inhibitory activity.
Keywords:
Carbonic anhyrases; Glycomimetic; Sulfonamidoglycosylation.
Copyright © 2016 Elsevier Ltd. All rights reserved.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Carbonic Anhydrase I / antagonists & inhibitors
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Carbonic Anhydrase I / metabolism*
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Carbonic Anhydrase II / antagonists & inhibitors
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Carbonic Anhydrase II / metabolism*
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Carbonic Anhydrase Inhibitors / chemical synthesis*
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Carbonic Anhydrase Inhibitors / chemistry
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Carbonic Anhydrase Inhibitors / metabolism
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Humans
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Neoplasms / metabolism
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Neoplasms / pathology
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Phenols / chemistry*
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Protein Binding
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Protein Isoforms / antagonists & inhibitors
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Protein Isoforms / metabolism
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Structure-Activity Relationship
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Sulfonamides / chemical synthesis
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Sulfonamides / chemistry*
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Sulfonamides / metabolism
Substances
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Carbonic Anhydrase Inhibitors
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Phenols
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Protein Isoforms
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Sulfonamides
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Carbonic Anhydrase I
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Carbonic Anhydrase II