New 3-O-glycosyl-3-demethylthiocolchicines containing natural and unnatural sugar moieties were prepared and tested on ç-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
Novel 3-O-glycosyl-3-demethylthiocolchicines as ligands for glycine and gamma-aminobutyric acid receptors / M.L. Gelmi, G. Fontana, D. Pocar, G. Pontremoli, S. Pellegrino, E. Bombardelli, A. Riva, W. Balduini, S. Carloni, M. Cimino. - In: JOURNAL OF MEDICINAL CHEMISTRY. - ISSN 0022-2623. - 50:9(2007), pp. 2245-2248.
Novel 3-O-glycosyl-3-demethylthiocolchicines as ligands for glycine and gamma-aminobutyric acid receptors
M.L. GelmiPrimo
;D. Pocar;G. Pontremoli;S. Pellegrino;
2007
Abstract
New 3-O-glycosyl-3-demethylthiocolchicines containing natural and unnatural sugar moieties were prepared and tested on ç-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
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