114081-67-3Relevant academic research and scientific papers
New synthesis of 3-(β-D-glucopyranosyl)-5-substituted-1,2,4-triazoles, nanomolar inhibitors of glycogen phosphorylase
Kun, Sándor,Bokor, éva,Varga, Gergely,Szocs, Béla,Páhi, András,Czifrák, Katalin,Tóth, Marietta,Juhász, László,Docsa, Tibor,Gergely, Pál,Somsák, László
, p. 567 - 579 (2014/04/03)
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
-
Page/Page column 25, (2013/05/21)
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.˙
Parallel copper catalysis: Diastereoselective synthesis of polyfunctionalized azetidin-2-imines
Xing, Yanpeng,Zhao, Hongyang,Shang, Qiongyi,Wang, Jing,Lu, Ping,Wang, Yanguang
supporting information, p. 2668 - 2671 (2013/07/19)
An efficient and diastereoselective synthesis of highly functionalized azetidin-2-imines has been achieved through a parallel catalysis strategy, including a copper-catalyzed azide-alkyne cycloaddition, a copper-catalyzed Csp-Csp2 cr
Tandem synthesis of 1-(alkylamino)-2,4-diarylpyrimido[6,1-a]isoquinolin-5-ium chlorides from isoquinoline, N-alkyl-benzimidoyl chlorides, and isocyanides
Yavari, Issa,Khalili, Gholamhossein,Mirzaei, Anvar
experimental part, p. 1190 - 1192 (2010/04/23)
1-(Alkylamino)-2,4-diarylpyrimido[6,1-a]isoquinolin-5-ium chlorides are obtained in good yields via a tandem reaction between isoquinoline, N-alkyl-benzimidoyl chlorides and alkyl isocyanides in anhydrous acetonitrile.
