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 (amides, ureas, carbamates, etc.). Included are the syntheses and physicochemical characterizations of some model sulfenamides to illustrate the promise of this new prodrug technology.
Guarino
Victor R
VR
Department of Pharmaceutical Chemistry, The University of Kansas, Lawrence, KS 66047, USA.
Karunaratne
Veranja
V
Stella
Valentino J
VJ
D000577:Amides / Q000737:chemistry / Q000494:pharmacology; D000588:Amines / Q000737:chemistry; D055598:Chemical Phenomena; D002621:Chemistry; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D015195:Drug Design; D006863:Hydrogen-Ion Concentration; D006868:Hydrolysis; D007700:Kinetics; D008956:Models, Chemical; D011355:Prodrugs / Q000737:chemistry* / Q000494:pharmacology; D013455:Sulfur / Q000737:chemistry*; D013696:Temperature
D000577:Amides; D000588:Amines; D011355:Prodrugs; D013455:Sulfur