Visible-Light-Triggered Release of Nitric Oxide from N-Pyramidal Nitrosamines

被引:42
|
作者
Karaki, Fumika [1 ]
Kabasawa, Yoji [1 ]
Yanagimoto, Takahiro [1 ]
Umeda, Nobuhiro [1 ]
Firman [1 ]
Urano, Yasuteru [2 ]
Nagano, Tetsuo [1 ]
Otani, Yuko [1 ]
Ohwada, Tomohiko [1 ]
机构
[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
[2] Univ Tokyo, Grad Sch Med, Bunkyo Ku, Tokyo 1130033, Japan
基金
日本学术振兴会;
关键词
cage compounds; cleavage reactions; nitrogen oxides; nitrosamines; photolysis; AMINO-ACID BEARING; COMPLEXES; NITROSYLS; STRATEGY; DESIGN; AMIDES; PLACE; TIME;
D O I
10.1002/chem.201101427
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Although many organic/inorganic compounds that release nitric oxide (NO) upon photoirradiation (phototriggered caged-NOs) have been reported, their photoabsorption wavelengths mostly lie in the UV region, because X?NO bonds (X=heteroatom and metal) generally have rather strong p-bond character. Thus, it is intrinsically difficult to generate organic compounds that release NO under visible light irradiation. Herein, the structures and properties of N-pyramidal nitrosamine derivatives of 7-azabicyclo[2.2.1]heptanes that release NO under visible light irradiation are described. Bathochromic shifts of the absorptions of these nitrosamines, attributed to HOMO (n)LUMO (p*) transitions associated with the nonplanar structure of the N?NO moiety, enable the molecules to absorb visible light, which results in N?NO bond cleavage. Thus, these compounds are innate organic caged-NOs that are uncaged by visible light.
引用
收藏
页码:1127 / 1141
页数:15
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