Simplification of adenophostin A defines a minimal structure for potent glucopyranoside-based mimics of D-myo-inositol 1,4,5-trisphosphate

Bioorg Med Chem Lett. 1999 Feb 8;9(3):453-8. doi: 10.1016/s0960-894x(99)00006-2.

Abstract

The synthesis of 1-O-[(3S,4R)-3-hydroxytetrahydrofuran-4-yl]-alpha-D-glucopyranosid e 3,4,3'-trisphosphate (7), a novel Ca2+ mobilising agonist at the Ins(1,4,5)P3 receptor, designed by excision of two motifs of adenophostin A is reported, defining a potential minimal structure for potent glucopyranoside-based agonists of Ins(1,4,5)P3 receptors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine / analogs & derivatives*
  • Adenosine / chemistry
  • Animals
  • Calcium / metabolism
  • Carbohydrate Conformation
  • Cells, Cultured
  • Furans / chemistry*
  • Furans / pharmacology
  • Glucosephosphates / chemistry*
  • Glucosephosphates / pharmacology
  • Glycosides / chemistry*
  • Inositol 1,4,5-Trisphosphate / chemistry*
  • Liver / cytology
  • Liver / drug effects
  • Liver / metabolism
  • Molecular Mimicry*
  • Rats

Substances

  • 1-O-(3-hydroxytetrahydrofuran-4-yl)glucopyranoside 3,4,3'-trisphosphate
  • Furans
  • Glucosephosphates
  • Glycosides
  • adenophostin A
  • Inositol 1,4,5-Trisphosphate
  • Adenosine
  • Calcium