De Novo Synthesis and Biological Evaluation of C6″-Substituted C4″-Amide Analogues of SL0101
| Autor: | Qi Zhang, Roman M. Mrozowski, Bulan Wu, Deborah A. Lannigan, Rajender Vemula, Zachary M. Sandusky, George A. O'Doherty |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2014 |
| Předmět: |
Glycosylation
Letter Stereochemistry Protein Serine-Threonine Kinases Biochemistry Ribosomal Protein S6 Kinases 90-kDa Ribosomal s6 kinase chemistry.chemical_compound Structure-Activity Relationship In vivo Amide Structure–activity relationship Monosaccharide Benzopyrans Physical and Theoretical Chemistry chemistry.chemical_classification Protein-Serine-Threonine Kinases biology Molecular Structure Organic Chemistry Monosaccharides Amides De novo synthesis chemistry biology.protein Half-Life |
| Zdroj: | Organic Letters |
| ISSN: | 1523-7052 1523-7060 |
| Popis: | In an effort to improve upon the in vivo half-life of the known ribosomal s6 kinase (RSK) inhibitor SL0101, C4″-amide/C6″-alkyl substituted analogues of SL0101 were synthesized and evaluated in cell-based assays. The analogues were prepared using a de novo asymmetric synthetic approach, which featured Pd-π-allylic catalyzed glycosylation for the introduction of a C4″-azido group. Surprisingly replacement of the C4″-acetate with a C4″-amide resulted in analogues that were no longer specific for RSK in cell-based assays. |
| Databáze: | OpenAIRE |
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