A novel class of 3-demethoxy-3-glycosylaminothiocolchicines ( 7) was prepared and tested for muscle relaxant activity. The syntheses were performed starting from the new 3-amino-3-demethoxythiocolchicine ( 5) prepared in good yield from 3-O-demethylthiocolchicine ( 1c) using the Buchwald-Hartwig reaction. The condensation of 5 with a series of pentose and hexose sugars ( 6) gave a series of 3-demethoxy-3-glycosylaminothiocolchicines ( 7). Their preparation was accomplished by adapting and improving a previous procedure for the preparation of N-arylglycosylamines. In particular, replacing traditional heating with microwave irradiation represents the key improvement of the process. The biological activity of the 3-demethoxy-3-glycosylaminothiocolchicines ( 7) was evaluated on GABA and strychnine-sensitive glycine receptors present in rat brain and spinal cord.
3-Demetoxy-3-glycosylaminothiocolchicines: synthesis of a new class of putative muscle relaxant compounds.
BALDUINI, WALTER;CARLONI, SILVIA;CIMINO, MAURO;
2006
Abstract
A novel class of 3-demethoxy-3-glycosylaminothiocolchicines ( 7) was prepared and tested for muscle relaxant activity. The syntheses were performed starting from the new 3-amino-3-demethoxythiocolchicine ( 5) prepared in good yield from 3-O-demethylthiocolchicine ( 1c) using the Buchwald-Hartwig reaction. The condensation of 5 with a series of pentose and hexose sugars ( 6) gave a series of 3-demethoxy-3-glycosylaminothiocolchicines ( 7). Their preparation was accomplished by adapting and improving a previous procedure for the preparation of N-arylglycosylamines. In particular, replacing traditional heating with microwave irradiation represents the key improvement of the process. The biological activity of the 3-demethoxy-3-glycosylaminothiocolchicines ( 7) was evaluated on GABA and strychnine-sensitive glycine receptors present in rat brain and spinal cord.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
