1187735-07-4Relevant academic research and scientific papers
Glucose-based spiro-heterocycles as potent inhibitors of glycogen phosphorylase
Nagy, Veronika,Benltifa, Mahmoud,Vidal, Sebastien,Berzsenyi, Eszter,Teilhet, Cathie,Czifrak, Katalin,Batta, Gyula,Docsa, Tibor,Gergely, Pal,Somsak, Laszlo,Praly, Jean-Pierre
experimental part, p. 5696 - 5707 (2009/12/05)
Glucopyranosylidene-spiro-1,4,2-oxathiazoles were prepared in high yields by NBS-mediated spiro-cyclization of the corresponding glucosyl-hydroximothioates. In an effort to synthesize analogous glucopyranosylidene-spiro-1,2,4-oxadiazolines, with a nitrogen atom instead of the sulphur, attempted cyclizations resulted in aromatization of the heterocycle with opening of the pyranosyl ring. Enzymatic measurements showed that some of the glucose-based inhibitors were active in the micromolar range. The 2-naphthyl-substituted 1,4,2-oxathiazole displayed the best inhibition against RMGPb (Ki = 160 nM), among glucose-based inhibitors known to date.
