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

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.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Gelmi ML,Pocar D,Pontremoli G,Pellegrino S,Bombardelli E,Fontana G,Riva A,Balduini W,Carloni S,Cimino M,Johnson F

doi

10.1021/jm060585t

subject

Has Abstract

pub_date

2006-09-07 00:00:00

pages

5571-7

issue

18

eissn

0022-2623

issn

1520-4804

journal_volume

49

pub_type

杂志文章

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