rdf:type |
|
lifeskim:mentions |
umls-concept:C0031711,
umls-concept:C0205314,
umls-concept:C0205474,
umls-concept:C0220781,
umls-concept:C0220908,
umls-concept:C0243071,
umls-concept:C0243077,
umls-concept:C0526812,
umls-concept:C0600115,
umls-concept:C0679622,
umls-concept:C0917785,
umls-concept:C1883254,
umls-concept:C2603343
|
pubmed:issue |
7
|
pubmed:dateCreated |
1998-11-4
|
pubmed:abstractText |
The synthesis and biochemical screening of four novel spironucleosides 1-4 against rabbit liver glycogen phosphorylase b (Gpb), along with molecular modeling studies on compound 2 and its 4-hydroxy analogue VII, have been presented. Gpb is a key enzyme of glycogen metabolism, and is known to be involved in the control of diabetes mellitus. The general strategy for synthesis involved base-catalyzed condensation of diethyl 2,4-dioxoimidazolidine-5-phosphonate (5) with either 2-deoxy-D-ribose or D-ribose, followed by sequential reactions involving ring-closure with phenylselenenyl chloride and reduction with tri-n-butyltin hydride catalyzed by azobisisobutyronitrile. Compounds 2 and 4 were found to be weak competitive inhibitors of Gpb, whereas 1 and 3 were inactive.
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pubmed:grant |
|
pubmed:language |
eng
|
pubmed:journal |
|
pubmed:citationSubset |
IM
|
pubmed:chemical |
|
pubmed:status |
MEDLINE
|
pubmed:month |
Jul
|
pubmed:issn |
0968-0896
|
pubmed:author |
|
pubmed:issnType |
Print
|
pubmed:volume |
6
|
pubmed:owner |
NLM
|
pubmed:authorsComplete |
Y
|
pubmed:pagination |
911-23
|
pubmed:dateRevised |
2007-11-14
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pubmed:meshHeading |
pubmed-meshheading:9730227-Animals,
pubmed-meshheading:9730227-Crystallography, X-Ray,
pubmed-meshheading:9730227-Enzyme Inhibitors,
pubmed-meshheading:9730227-Hydantoins,
pubmed-meshheading:9730227-Ligands,
pubmed-meshheading:9730227-Models, Molecular,
pubmed-meshheading:9730227-Muscle, Skeletal,
pubmed-meshheading:9730227-Nucleosides,
pubmed-meshheading:9730227-Phosphorylase b,
pubmed-meshheading:9730227-Protein Binding,
pubmed-meshheading:9730227-Rabbits,
pubmed-meshheading:9730227-Spiro Compounds
|
pubmed:year |
1998
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pubmed:articleTitle |
Inhibitors of glycogen phosphorylase b: synthesis, biochemical screening, and molecular modeling studies of novel analogues of hydantocidin.
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pubmed:affiliation |
Department of Chemistry and Biochemistry, University of Maryland, Baltimore County 21250, USA.
|
pubmed:publicationType |
Journal Article,
Research Support, U.S. Gov't, P.H.S.
|