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

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 gluco...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 1999-02, Vol.9 (3), p.453-458
Main Authors: MARWOOD, R. D, RILEY, A. M, CORREA, V, TAYLOR, C. W, POTTER, B. V. L
Format: Article
Language:English
Subjects:
Adenosine - analogs & derivatives
Adenosine - chemistry
Animals
Biological and medical sciences
Bones, joints and connective tissue. Antiinflammatory agents
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
Medical sciences
Molecular Mimicry
Pharmacology. Drug treatments
Rats
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Summary: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.
ISSN:0960-894X
1464-3405
DOI:10.1016/S0960-894X(99)00006-2