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
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.
3-demethoxy-3-glycosylaminothiocolchicines: synthesis of a new class of putative muscle relaxant compounds
M.L. GelmiPrimo
;D. PocarSecondo
;G. Pontremoli;S. Pellegrino;
2006
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 cordPubblicazioni consigliate
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