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Regio- and diastereoselective construction of α-hydroxy-δ-amino ester derivatives via 1,4-conjugate addition of β,γ-unsaturated N-sulfonylimines.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2014 May 02; Vol. 79 (9), pp. 4142-7. Date of Electronic Publication: 2014 Apr 15. - Publication Year :
- 2014
-
Abstract
- A first example of 1,4-conjugate addition of β,γ-unsaturated N-sulfonylimines via the oxonium ylides trapping process was developed. This method afforded a novel and efficient access for the high regio- and diastereoselective construction of α-hydroxyl-δ-amino esters derivatives, which exhibit inhibitory activity on PTP1B and SIRT1 enzymes in vitro. The synthetic potentials and the biological activity of the resulting products were well demonstrated to be promising for drug discovery.
- Subjects :
- Dose-Response Relationship, Drug
Enzyme Inhibitors chemical synthesis
Enzyme Inhibitors chemistry
Esters
Molecular Structure
Protein Tyrosine Phosphatase, Non-Receptor Type 1 metabolism
Sirtuin 1 metabolism
Stereoisomerism
Structure-Activity Relationship
Enzyme Inhibitors pharmacology
Imines chemistry
Protein Tyrosine Phosphatase, Non-Receptor Type 1 antagonists & inhibitors
Sirtuin 1 antagonists & inhibitors
Sulfones chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 79
- Issue :
- 9
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 24689439
- Full Text :
- https://doi.org/10.1021/jo500176g