Synthesis of heterocyclic N-(b-D-gluco of glycogen phosphorylase
نویسندگان
چکیده
In a DCC-mediated cou N-propynoyl-2,3,4,6-tet cycloadditions with aro copyranosyl)-1-substitu isoxazole-5-carboxamid to be tested as inhibitor were N-(b-D-glucopyra N-(b-D-glucopyranosyl)1
منابع مشابه
Synthesis of New C- and N-β-d-Glucopyranosyl Derivatives of Imidazole, 1,2,3-Triazole and Tetrazole, and Their Evaluation as Inhibitors of Glycogen Phosphorylase.
The aim of the present study was to broaden the structure-activity relationships of C- and N-β-d-glucopyranosyl azole type inhibitors of glycogen phosphorylase. 1-Aryl-4-β-d-gluco-pyranosyl-1,2,3-triazoles were prepared by copper catalyzed azide-alkyne cycloadditions between O-perbenzylated or O-peracetylated β-d-glucopyranosyl ethynes and aryl azides. 1-β-d-Gluco-pyranosyl-4-phenyl imidazole w...
متن کاملSTEREOSELECTIVE SYNTHESIS OF METHYL TETRA-0-METHYL a-AND P-D-GLUCO-AND MANNOPYRANOSIDES
Methyl tetra - 0-methyl- ?-D- glucopyranoside is stereoselectively prepared from tetramethyl-D- glucopyranose by using (MeI+NaH) in toluene (86%) or cyclohexane (85%), while its ?- isomer is best synthesized in hexamethyl phosphoramide (64%). Similarly, methyl tetra-o-methyl-?- D-mannopyranoside is synthesized in cyclohexane (80%), while its ?- isomer is predominantly prepared by (MeI+n-Bu...
متن کاملNew 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-triazol...
متن کاملSynthesis of 2-(β-D-glucopyranosyl)-5-(substituted-amino)-1,3,4-oxa- and -thiadiazoles for the inhibition of glycogen phosphorylase.
O-Perbenzoylated 4-phenyl-[C-(β-d-glucopyranosyl)formaldehyde]semicarbazone was prepared in the reaction of O-perbenzoylated β-d-glucopyranosyl cyanide and 4-phenylsemicarbazide in the presence of Raney-Ni. Acylation of O-perbenzoylated C-(β-d-glucopyranosyl)formaldehyde semicarbazone furnished the corresponding 4-acyl-[C-(β-d-glucopyranosyl)formaldehyde]semicarbazones. The reaction of O-perben...
متن کاملHepatic glycogen synthesis is highly sensitive to phosphorylase activity: evidence from metabolic control analysis.
We used metabolic control analysis to determine the flux control coefficient of phosphorylase on glycogen synthesis in hepatocytes by titration with a specific phosphorylase inhibitor (CP-91149) or by expression of muscle phosphorylase using recombinant adenovirus. The muscle isoform was used because it is catalytically active in the b-state. CP-91149 inactivated phosphorylase with sequential a...
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