331258-39-0Relevant articles and documents
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
experimental part, 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
New synthesis of 7-azabicyclo[2.2.1]heptane-1-carboxylic acid
Avenoza, Alberto,Cativiela, Carlos,Busto, Jesús H,Fernández-Recio, Miguel A,Peregrina, Jesús M,Rodríguez, Fernando
, p. 545 - 548 (2007/10/03)
This report describes a new synthetic route to 7-azabicyclo[2.2.1]heptane-1-carboxylic acid (Ahc), a constrained proline analogue, in which the key step is the Diels-Alder reaction using methyl 2-benzamidoacrylate as dienophile.
New synthesis of all four 1-amino-2-hydroxycyclohexanecarboxylic acids
Avenoza,Barriobero,Cativiela,Fernández-Recio,Peregrina,Rodríguez
, p. 2745 - 2755 (2007/10/03)
This report describes a new synthesis of the four stereoisomers of 1-amino-2-hydroxycyclohexanecarboxylic acids [(1S,2S)-, (1R,2R)-, (1S,2R)- and (1R,2S)-c6Ser], four conformationally constrained serine (Ser) analogues, possessing a six-membere
