A Synthesis of a Spirocyclic Macrocyclic Protease Inhibitor for the Treatment of Hepatitis C
| Autor: | Aaron M. Dumas, Peter E. Maligres, Michael Shevlin, Rebecca T. Ruck, Cheol K. Chung, Ed Cleator, Andrew Nolting, Jacqueline D. Hicks, Guy R. Humphrey, Nelo R. Rivera |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
Aluminum foil
Macrocyclic Compounds Stereochemistry chemistry.chemical_element Zinc Hepacivirus Viral Nonstructural Proteins 010402 general chemistry 01 natural sciences Biochemistry Antiviral Agents Heterocyclic Compounds 4 or More Rings Structure-Activity Relationship Drug Discovery medicine Spiro Compounds Physical and Theoretical Chemistry Molecular Structure 010405 organic chemistry Chemistry Drug discovery Drug candidate Organic Chemistry Carbonyl reduction Hepatitis C Protease inhibitor (biology) 0104 chemical sciences Stereoselectivity medicine.drug |
| Zdroj: | Organic letters. 18(6) |
| ISSN: | 1523-7052 |
| Popis: | The development of a convergent and highly stereoselective synthesis of an HCV NS3/4a protease inhibitor possessing a unique spirocyclic and macrocyclic architecture is described. A late-stage spirocyclization strategy both enabled rapid structure–activity relationship studies in the drug discovery phase and simultaneously served as the basis for the large scale drug candidate preparation for clinical use. Also reported is the discovery of a novel InCl3-catalyzed carbonyl reduction with household aluminum foil or zinc powder as the terminal reductant. |
| Databáze: | OpenAIRE |
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