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-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.