Discovery, total synthesis, HRV 3C-protease inhibitory activity, and structure–activity relationships of 2-methoxystypandrone and its analogues
| Autor: | Pia L. Graham, Sheo B. Singh, Michael G Cordingley, Robert A. Reamer |
|---|---|
| Rok vydání: | 2001 |
| Předmět: |
Picornain 3C
Stereochemistry Clinical Biochemistry Pharmaceutical Science Biochemistry Chemical synthesis Structure-Activity Relationship Viral Proteins chemistry.chemical_compound Drug Discovery Protease Inhibitors Molecular Biology chemistry.chemical_classification biology Organic Chemistry 3C Viral Proteases Total synthesis Naphthoquinone In vitro Quinone Cysteine Endopeptidases Enzyme chemistry Enzyme inhibitor biology.protein Molecular Medicine Naphthoquinones |
| Zdroj: | Bioorganic & Medicinal Chemistry Letters. 11:3143-3146 |
| ISSN: | 0960-894X |
| DOI: | 10.1016/s0960-894x(01)00648-5 |
| Popis: | 2-Methoxystypandrone, a naphthoquinone, was isolated from a Chinese herb Polygonum cuspidatum by bioassay guided fractionation using HRV 3C-protease assay. It showed an IC 50 value of 4.6 μM and is moderately selective. A new 10-step, total synthesis of 2-methoxystypandrone was accomplished in 45% overall yield using a Diels–Alder approach. Several analogues of this compound were prepared. Isolation, synthesis and HRV 3C-protease structure–activity relationships of these compounds have been described. |
| Databáze: | OpenAIRE |
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