An efficient, asymmetric solid-phase synthesis of benzothiadiazine-substituted tetramic acids: Potent inhibitors of the hepatitis C virus RNA-dependent RNA polymerase
| Autor: | George Burton, Karen A. Evans, Ralph A. Rivero, Deping Chai, Robert T. Sarisky, Juili Lin-Goerke, Todd L. Graybill, Victor K. Johnston |
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| Rok vydání: | 2006 |
| Předmět: |
Stereochemistry
Hepatitis C virus Clinical Biochemistry Pharmaceutical Science Hepacivirus Benzothiadiazines medicine.disease_cause Antiviral Agents Biochemistry Reductive amination Chemical synthesis Catalysis Inhibitory Concentration 50 chemistry.chemical_compound Solid-phase synthesis RNA polymerase Drug Resistance Viral Drug Discovery medicine Animals Humans Molecular Biology Amination Organic Chemistry Enantioselective synthesis RNA-Dependent RNA Polymerase Hepatitis C Pyrrolidinones chemistry Cyclization Benzothiadiazine Molecular Medicine |
| Zdroj: | Bioorganic & Medicinal Chemistry Letters. 16:2205-2208 |
| ISSN: | 0960-894X |
| Popis: | An efficient, asymmetric solid-phase synthesis of benzothiadiazine-substituted tetramic acids is reported. Starting from commercially available chiral Fmoc-protected alpha-amino acids loaded onto Wang resin, Fmoc removal, reductive amination followed by amide bond formation, and base-catalyzed cyclization with simultaneous cleavage from the resin provided the desired products. Compounds described are potent inhibitors of the hepatitis C virus RNA-dependent RNA polymerase. |
| Databáze: | OpenAIRE |
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