Schmidt M, Eger K
Universität Leipzig, Institut für Pharmazie, Germany.
Pharmazie. 1996 Jan;51(1):11-6.
The nitrostyrene derivatives 1a-m, prepared by the reaction of nitromethane with the appropriate substituted benzaldehyde, were reacted with ascorbic acid in a Michael type reaction to the new compounds 2a-h. The structural assignment of the resulting mixture of diastereomers could be performed by means of two dimensional homo- and heterocorrelated NMR spectroscopy and comparison to known Michael adducts of ascorbic acid. Catalytic hydrogenolysis of 2a yielded the rearranged compound 7, formed by intramolecular aminolysis in analogy to the rearrangement of the Michael adduct of ascorbic acid and methylvinylketone 3 given in the literature. On testing, the C-nucleoside 7 did not reveal virostatic or cytostatic effects.
通过硝基甲烷与适当取代的苯甲醛反应制备的硝基苯乙烯衍生物1a - m，在迈克尔型反应中与抗坏血酸反应生成新化合物2a - h。所得非对映异构体混合物的结构归属可通过二维同核和异核相关核磁共振光谱法以及与已知的抗坏血酸迈克尔加合物进行比较来完成。2a的催化氢解产生了重排化合物7，其通过分子内氨解形成，类似于文献中给出的抗坏血酸与甲基乙烯基酮3的迈克尔加合物的重排。经测试，碳核苷7没有显示出抗病毒或细胞抑制作用。
