Development of carbamate-tethered coumarins as phototriggers for caged nicotinamide

被引：15

作者：

Bourbon, Pauline ^{[1
]}

Peng, Qian ^{[1
]}

Ferraudi, Guillermo ^{[1
,2
]}

Stauffacher, Cynthia ^{[3
]}

Wiest, Olaf ^{[1
]}

Helquist, Paul ^{[1
]}

机构：

[1] Univ Notre Dame, Dept Chem & Biochem, Notre Dame, IN 46556 USA

[2] Notre Dame Radiat Res Lab, Notre Dame, IN 46556 USA

[3] Purdue Univ, Dept Biol Sci, W Lafayette, IN 47907 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2013年 / 23卷 / 23期

关键词：

Caged compound; Nicotinamide; Coumarin; Photocleavage; PHOTOLABILE PROTECTING GROUP; CHEMISTRY;

D O I：

10.1016/j.bmcl.2013.09.067

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

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. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：6321 / 6324

页数：4

共 23 条

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