3-demethoxy-3-glycosylaminothiocolchicines: synthesis of a new class of putative muscle relaxant compounds

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