Novel 3-O-Glycosyl-3-demethylthiocolchicines as Ligands for Glycine and γ-Aminobutyric Acid Receptors

New 3-O-glycosyl-3-demethylthiocolchicines containing natural and unnatural sugar moieties were prepared and tested on γ-aminobutyric acid (GABA) and strychnine-sensitive glycine receptors present in rat brain and spinal cord. Two different synthetic approaches were used with the readily available 3...

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Bibliographic Details
Published in:Journal of medicinal chemistry 2007-05, Vol.50 (9), p.2245-2248
Main Authors: Gelmi, Maria Luisa, Fontana, Gabriele, Pocar, Donato, Pontremoli, Guido, Pellegrino, Sara, Bombardelli, Ezio, Riva, Antonella, Balduini, Walter, Carloni, Silvia, Cimino, Mauro
Format: Article
Language:English
Subjects:
Animals
Binding Sites
Biological and medical sciences
Brain - metabolism
Colchicine - analogs & derivatives
Colchicine - chemical synthesis
Colchicine - pharmacology
Gabaergic and benzodiazepinic system
Glutamatergic system (aspartate and other excitatory aminoacids)
Glycosides - chemical synthesis
Glycosides - pharmacology
In Vitro Techniques
Ligands
Medical sciences
Muscimol - pharmacology
Neuropharmacology
Neurotransmitters. Neurotransmission. Receptors
Pharmacology. Drug treatments
Radioligand Assay
Rats
Rats, Sprague-Dawley
Receptors, GABA - metabolism
Receptors, Glycine - metabolism
Spinal Cord - metabolism
Structure-Activity Relationship
Strychnine - pharmacology
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Summary:New 3-O-glycosyl-3-demethylthiocolchicines containing natural and unnatural sugar moieties were prepared and tested on γ-aminobutyric acid (GABA) and strychnine-sensitive glycine receptors present in rat brain and spinal cord. Two different synthetic approaches were used with the readily available 3-O-demethylthiocolchicine (1b) and thiocolchicoside (2a). Glycosyl compounds 2a − g were obtained from 1b and 1-fluorosugars 4. 6‘-Heterosubstituted glycosyl compounds 6−12 and the 6‘-desoxy derivative 2h were prepared from 2a.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm061056s