Sulfenamides as prodrugs of NH-acidic compounds: A new prodrug option for the amide bond

Sulfenamides as prodrugs of NH-acidic compounds: A new prodrug option for the amide bond

The objective of this report is to introduce the novel concept of utilizing sulfenamides as prodrugs for compounds containing an NH-acidic functionality, particularly weakly acidic amide-type functionalities. The objective of this report is to introduce the novel concept of utilizing sulfenamides as...

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Veröffentlicht in:Bioorganic & medicinal chemistry letters 2007-09, Vol.17 (17), p.4910-4913
Hauptverfasser: Guarino, Victor R., Karunaratne, Veranja, Stella, Valentino J.
Format: Artikel
Sprache:eng
Schlagworte:
Amide
Amides - chemistry
Amides - pharmacology
Amines - chemistry
Bioavailability
Biological and medical sciences
Chemical Phenomena
Chemistry
Chemistry, Pharmaceutical - methods
Dissolution rate
Drug Design
Hydrogen-Ion Concentration
Hydrolysis
Kinetics
Medical sciences
Miscellaneous
Models, Chemical
NH-acid
Permeability
Pharmacology. Drug treatments
Prodrug
Prodrugs - chemistry
Prodrugs - pharmacology
Solubility
Stability
Sulfenamide
Sulfur - chemistry
Temperature
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Zusammenfassung:The objective of this report is to introduce the novel concept of utilizing sulfenamides as prodrugs for compounds containing an NH-acidic functionality, particularly weakly acidic amide-type functionalities. The objective of this report is to introduce the novel concept of utilizing sulfenamides as prodrugs for compounds containing an NH-acidic functionality, particularly weakly acidic amide-type functionalities (amides, ureas, carbamates, etc.). Included are the syntheses and physicochemical characterizations of some model sulfenamides to illustrate the promise of this new prodrug technology.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2007.06.037