943620-86-8Relevant articles and documents
Synthesis of 7-azabicyclo[2.2.1]heptane-1,4-dicarboxylic acid, a rigid non-chiral analogue of 2-aminoadipic acid
Kubyshkin, Vladimir S.,Mikhailiuk, Pavel K.,Komarov, Igor V.
, p. 4061 - 4063 (2007)
A non-chiral, rigid 7-azabicyclo[2.2.1]heptane-1,4-dicarboxylic acid, an analogue of 2-aminoadipic acid, has been synthesized in six steps from dimethyl-meso-2,5-dibromohexanedioate in 28% total yield. A key step in the synthesis is double alkylation of a
Visible-light-triggered release of nitric oxide from N-pyramidal nitrosamines
Karaki, Fumika,Kabasawa, Yoji,Yanagimoto, Takahiro,Umeda, Nobuhiro,Firman,Urano, Yasuteru,Nagano, Tetsuo,Otani, Yuko,Ohwada, Tomohiko
, p. 1127 - 1141 (2012/03/26)
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 π-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 (π*) 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. A visible difference: Nitrosamine derivatives of 7-azabicyclo[2.2.1]heptanes undergo N - NO bond cleavage upon exposure to visible light at wavelengths longer than 420a nm, thereby releasing NO. Bathochromic shifts of the absorptions of these nitrosamines are attributed to HOMO (n)-LUMO (π*) transitions associated with the nonplanar structure of the N - NO moiety (see figure). Copyright
