1430730-45-2

Upstream product

• 2243-83-6 2-naphthaloyl chloride 
• 149358-58-7 N-benzylnaphthalene-2-carboxamide 
• 706784-62-5 5-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)tetrazole 

Downstream Products

• 1430730-61-2 4-benzyl-5-(β-D-glucopyranosyl)-3-(2-naphthyl)-1,2,4-triazole 

Relevant academic research and scientific papers

New synthesis of 3-(β-D-glucopyranosyl)-5-substituted-1,2,4-triazoles, nanomolar inhibitors of glycogen phosphorylase

O-Perbenzoylated 5-(β-D-glucopyranosyl)tetrazole was reacted with N-benzyl carboximidoyl chlorides to give the corresponding 4-benzyl-3-(β-D- glucopyranosyl)-5-substituted-1,2,4-triazoles. Removal of the O-benzoyl and N-benzyl protecting groups by base catalysed transesterification and catalytic hydrogenation, respectively, furnished a series of 3-(β-D-glucopyranosyl)- 5-substituted-1,2,4-triazoles with aliphatic, mono- and bicyclic aromatic, and heterocyclic substituents in the 5-position. Enzyme kinetic studies revealed these compounds to inhibit rabbit muscle glycogen phosphorylase b: best inhibitors were the 5-(4-aminophenyl)- (Ki 0.67 μM) and the 5-(2-naphthyl)-substituted (Ki 0.41 μM) derivatives. This study uncovered the C-glucopyranosyl-1,2,4-triazoles as a novel skeleton for nanomolar inhibition of glycogen phosphorylase.

GLYCOGEN PHOSPHORYLASE INHIBITORS

The invention relates to compounds of formula (I) and stereoisomers, tautomers and pharmaceutically acceptable salts thereof and processes for preparing them. In formula (I) X is -CH= or -N= or -N(R") -; Y is -N= or -N(R") -; R is an alkyl group, an aryl group or a heteroaryl group, which groups are unsubstituted or substituted; R' is hydrogen or PG1, R" is hydrogen or PG2, R"' is hydrogen or R'OCH2-; n is an integer of 1 to 3. The invention also relates to pharmaceutical compositions containing these compounds. The compounds according to the invention are glycogen phosphorylase inhibitors and can be used e.g. for the treatment of type 2 diabetes, cardiovascular disorders and tumorous growth.˙