Abstract
New 3-O-glycosyl-3-demethylthiocolchicines containing natural and unnatural sugar moieties were prepared and tested on gamma-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.
MeSH terms
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Animals
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Binding Sites
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Brain / metabolism
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Colchicine / analogs & derivatives*
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Colchicine / chemical synthesis*
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Colchicine / pharmacology
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Glycosides / chemical synthesis*
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Glycosides / pharmacology
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In Vitro Techniques
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Ligands
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Muscimol / pharmacology
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Radioligand Assay
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Rats
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Rats, Sprague-Dawley
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Receptors, GABA / metabolism*
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Receptors, Glycine / metabolism*
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Spinal Cord / metabolism
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Structure-Activity Relationship
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Strychnine / pharmacology
Substances
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Glycosides
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Ligands
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Receptors, GABA
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Receptors, Glycine
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Muscimol
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Strychnine
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Colchicine