Abstract
A mild, efficient and one pot procedure to access benzoxazoles using easily accessible acylselenoureas as starting materials has been discovered. Mechanistic studies revealed a pH dependent intramolecular oxidative deselenization, with ring closure due to an intramolecular nucleophilic attack of a phenoxide ion. All the benzoxazoles herein reported possessed a primary sulfonamide zinc binding group and showed effective inhibitory action on the enzymes, carbonic anhydrases.
MeSH terms
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Amides / chemical synthesis
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Amides / chemistry
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Amides / pharmacology*
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Benzoxazoles / chemical synthesis
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Benzoxazoles / chemistry
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Benzoxazoles / pharmacology*
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Carbonic Anhydrase Inhibitors / chemical synthesis
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Carbonic Anhydrase Inhibitors / chemistry
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Carbonic Anhydrase Inhibitors / pharmacology*
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Carbonic Anhydrases / metabolism*
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Dose-Response Relationship, Drug
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Humans
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Molecular Structure
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Organoselenium Compounds / chemistry*
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Oxidation-Reduction
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Structure-Activity Relationship
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Urea / analogs & derivatives*
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Urea / chemistry
Substances
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Amides
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Benzoxazoles
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Carbonic Anhydrase Inhibitors
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Organoselenium Compounds
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selenourea
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Urea
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Carbonic Anhydrases