| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 10591298 | Bioorganic & Medicinal Chemistry Letters | 2013 | 4 Pages |
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.
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Authors
Pauline Bourbon, Qian Peng, Guillermo Ferraudi, Cynthia Stauffacher, Olaf Wiest, Paul Helquist,