3-demethoxy-3-glycosylaminothiocolchicines: synthesis of a new class of putative muscle relaxant compounds
Articolo
Data di Pubblicazione:
2006
Citazione:
3-demethoxy-3-glycosylaminothiocolchicines: synthesis of a new class of putative muscle relaxant compounds / M.L. Gelmi, D. Pocar, G. Pontremoli, S. Pellegrino, E. Bombardelli, G. Fontana, A. Riva, W. Balduini, S. Carloni, M. Cimino, F. Johnson. - In: JOURNAL OF MEDICINAL CHEMISTRY. - ISSN 0022-2623. - 49:18(2006), pp. 5571-5577.
Abstract:
A novel class of 3-demethoxy-3-glycosylaminothiocolchicines was prepd. and tested for muscle relaxant activity. The syntheses were performed starting from the new 3-amino-3-demethoxythiocolchicine (I) prepd. in good yield from 3-O-demethylthiocolchicine using the Buchwald-Hartwig reaction. The condensation of I with a series of pentose and hexose sugars gave a series of 3-demethoxy-3-glycosylaminothiocolchicines. Their prepn. was accomplished by adapting and improving a previous procedure for the prepn. of N-arylglycosylamines. In particular, replacing traditional heating with microwave irradn. represents the key improvement of the process. The biol. activity of the 3-demethoxy-3-glycosylaminothiocolchicines was evaluated on GABA and strychnine-sensitive glycine receptors present in rat brain and spinal cord
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
3-demethoxy-3-glycosylaminothiocolchicines; putative muscle relaxant compds.; via microwave irradn. condensation of 3-amino-3-demethoxythiocolchicine with monosaccharides); Brain; Condensation reaction; Coupling reaction; Glycosylation; GABA receptors; Glycine receptors Role: BSU (Biological study, unclassified), BIOL (Biological study) Monosaccharides Role: RCT (Reactant), RACT (Reactant or reagent)
Elenco autori:
M.L. Gelmi, D. Pocar, G. Pontremoli, S. Pellegrino, E. Bombardelli, G. Fontana, A. Riva, W. Balduini, S. Carloni, M. Cimino, F. Johnson
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