1430731-00-2

Upstream product

• 70-11-1 α-bromoacetophenone 
• 80300-30-7 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 500766-97-2 2,3,4,6-tetra-O-benzyl-α/β-D-glucopyranosyl cyanide 
• 85422-85-1 1-Deoxy-2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl cyanide 
• 1430730-98-5 4(5)-phenyl-2-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)imidazole 

Relevant academic research and scientific papers

Improved preparation of 4(5)-aryl-2-(β-d-glucopyranosyl)-imidazoles, the most efficient glucose analogue inhibitors of glycogen phosphorylase

The synthesis of 4(5)-aryl-2-(β-d-glucopyranosyl)-imidazoles, the currently most efficient glucose derived inhibitors of glycogen phosphorylase enzymes was amended and extended by using O-perbenzylated β-d-glucopyranosyl cyanide as the starting material.

4(5)-Aryl-2-C-glucopyranosyl-imidazoles as New Nanomolar Glucose Analogue Inhibitors of Glycogen Phosphorylase

Inhibition of glycogen phosphorylases may lead to pharmacological treatments of diseases in which glycogen metabolism plays an important role: first of all in diabetes, but also in cardiovascular and tumorous disorders. C-(β-d-Glucopyranosyl) isoxazole, pyrazole, thiazole, and imidazole type compounds were synthesized, and the latter showed the strongest inhibition against rabbit muscle glycogen phosphorylase b. Most efficient was 2-(β-d-glucopyranosyl)-4(5)-(2-naphthyl)-imidazole (11b, Ki = 31 nM) representing the best nanomolar glucose derived inhibitor of the enzyme.

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.˙