title: Novel 3-O-glycosyl-3-demethylthiocolchicines as ligands for glycine and gamma-aminobutyric acid receptors.
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.
authors.affiliation: Istituto di Chimica Organica "A. Marchesini", Facoltà di Farmacia, Università di Milano, Via Venezian 21, 20133 Milano, Italy. marialuisa.gelmi@unimi.it
authors.forename: Maria Luisa
authors.initials: ML
authors.lastname: Gelmi
authors.forename: Gabriele
authors.initials: G
authors.lastname: Fontana
authors.forename: Donato
authors.initials: D
authors.lastname: Pocar
authors.forename: Guido
authors.initials: G
authors.lastname: Pontremoli
authors.forename: Sara
authors.initials: S
authors.lastname: Pellegrino
authors.forename: Ezio
authors.initials: E
authors.lastname: Bombardelli
authors.forename: Antonella
authors.initials: A
authors.lastname: Riva
authors.forename: Walter
authors.initials: W
authors.lastname: Balduini
authors.forename: Silvia
authors.initials: S
authors.lastname: Carloni
authors.forename: Mauro
authors.initials: M
authors.lastname: Cimino
mesh_terms: D000818:Animals; D001665:Binding Sites; D001921:Brain / Q000378:metabolism; D003078:Colchicine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology; D006027:Glycosides / Q000138:chemical synthesis* / Q000494:pharmacology; D066298:In Vitro Techniques; D008024:Ligands; D009118:Muscimol / Q000494:pharmacology; D011869:Radioligand Assay; D051381:Rats; D017207:Rats, Sprague-Dawley; D018079:Receptors, GABA / Q000378:metabolism*; D018009:Receptors, Glycine / Q000378:metabolism*; D013116:Spinal Cord / Q000378:metabolism; D013329:Structure-Activity Relationship; D013331:Strychnine / Q000494:pharmacology
chemical_list: D006027:Glycosides; D008024:Ligands; D018079:Receptors, GABA; D018009:Receptors, Glycine; D009118:Muscimol; D013331:Strychnine; D003078:Colchicine