title: Synthesis of N-(beta-D-glucopyranosyl)- and N-(2-acetamido-2-deoxy-beta-D-glucopyranosyl) amides as inhibitors of glycogen phosphorylase.
abstract: 2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl- and 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyl azides were transformed into the corresponding per-O-acetylated N-(beta-D-glycopyranosyl) amides via a PMe(3) mediated Staudinger protocol (generation of N-(beta-D-glycopyranosyl)imino-trimethylphosphoranes followed by acylation with carboxylic acids, acid chlorides or anhydrides). The deprotected compounds obtained by Zemplén deacetylation were evaluated as inhibitors of rabbit muscle glycogen phosphorylase b. The best inhibitor of this series has been N-(beta-D-glucopyranosyl) 3-(2-naphthyl)-propenoic amide (K(i)=3.5microM).
authors.affiliation: Department of Organic Chemistry, Faculty of Science, PO Box 20, H-4010 Debrecen, Hungary.
authors.forename: Zoltán
authors.initials: Z
authors.lastname: Györgydeák
authors.forename: Zsuzsa
authors.initials: Z
authors.lastname: Hadady
authors.forename: Nóra
authors.initials: N
authors.lastname: Felföldi
authors.forename: Attila
authors.initials: A
authors.lastname: Krakomperger
authors.forename: Veronika
authors.initials: V
authors.lastname: Nagy
authors.forename: Marietta
authors.initials: M
authors.lastname: Tóth
authors.forename: Attila
authors.initials: A
authors.lastname: Brunyánszki
authors.forename: Tibor
authors.initials: T
authors.lastname: Docsa
authors.forename: Pál
authors.initials: P
authors.lastname: Gergely
authors.forename: László
authors.initials: L
authors.lastname: Somsák
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D005947:Glucose / Q000138:chemical synthesis* / Q000494:pharmacology; D024982:Glycogen Phosphorylase, Muscle Form / Q000037:antagonists & inhibitors* / Q000378:metabolism; D009539:Nicotinic Acids / Q000138:chemical synthesis* / Q000494:pharmacology; D011817:Rabbits
chemical_list: D000577:Amides; D004791:Enzyme Inhibitors; D009539:Nicotinic Acids; D024982:Glycogen Phosphorylase, Muscle Form; D005947:Glucose