C-(2-Deoxy-D-arabino-hex-1-enopyranosyl)-oxadiazoles: synthesis of possible isomers and their evaluation as glycogen phosphorylase inhibitors

Bokor, Éva and Szennyes, Eszter and Csupász, Tibor and Tóth, Nóra and Docsa, Tibor and Gergely, Pál and Somsák, László (2015) C-(2-Deoxy-D-arabino-hex-1-enopyranosyl)-oxadiazoles: synthesis of possible isomers and their evaluation as glycogen phosphorylase inhibitors. Carbohydrate Research, 412. pp. 71-79. ISSN 0008-6215

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Abstract

Synthetic methods were elaborated for D-glucals attached to oxadiazoles by a C-C bond. Introduction of the double bond was effected by either DBU induced elimination of PhCOOH from the O-perbenzoylated glucopyranosyl precursors or Zn/N-methylimidazole mediated reductive elimination from the 1-bromoglucopyranosyl starting compounds. Alternatively, heterocyclizations of 2-deoxy-D-arabino-hex-1-enopyranosyl cyanide were also carried out. Test compounds were obtained by Zemplén debenzoylation, however, none of them showed significant inhibition of rabbit muscle glycogen phosphorylase b.

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