title: Development of carbamate-tethered coumarins as phototriggers for caged nicotinamide.
abstract: The syntheses of 7-diethylaminocoumarin- or modified DEACM-nicotinamide and 6-bromo-7-methoxycoumarin- or BMCM-nicotinamide have been accomplished by reaction of nicotinoyl isocyanate with the corresponding coumarin allylic alcohol derivatives. The resulting compounds contain an N-acyl O-alkyl carbamate as a new type of linkage for the caging of nicotinamide with a coumarin phototrigger, which undergoes cleavage upon photolysis. Our design of specific caged-nicotinamides was based upon NBO and TD-FT calculations to predict absorption wavelengths and photocleavage potential. This work provides a potentially general method for the caging of amides with coumarin photolabile protecting groups.
authors.affiliation: Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, IN 46556, USA.
authors.forename: Pauline
authors.initials: P
authors.lastname: Bourbon
authors.forename: Qian
authors.initials: Q
authors.lastname: Peng
authors.forename: Guillermo
authors.initials: G
authors.lastname: Ferraudi
authors.forename: Cynthia
authors.initials: C
authors.lastname: Stauffacher
authors.forename: Olaf
authors.initials: O
authors.lastname: Wiest
authors.forename: Paul
authors.initials: P
authors.lastname: Helquist
mesh_terms: D002219:Carbamates / Q000138:chemical synthesis / Q000737:chemistry*; D003374:Coumarins / Q000138:chemical synthesis / Q000737:chemistry*; D009536:Niacinamide / Q000138:chemical synthesis / Q000737:chemistry*; D055668:Photochemical Processes
chemical_list: D002219:Carbamates; D003374:Coumarins; D009536:Niacinamide
keywords: Caged compound; Coumarin; Nicotinamide; Photocleavage