Alteration of the bis-tetrahydrofuran core stereochemistries in asimicin can affect the cytotoxicity
| Autor: | Subhash C. Sinha, Halina Pietraszkiewicz, Matthew Edelstein, Frederick Valeriote, Zheng Zheng Huang, Zhiyong Chen, Eiko Nakamaru-Ogiso |
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| Rok vydání: | 2008 |
| Předmět: |
Stereochemistry
Molecular Conformation Stereoisomerism Chemical synthesis Article chemistry.chemical_compound Mice Structure-Activity Relationship Cell Line Tumor Drug Discovery Structure–activity relationship Animals Humans Cytotoxicity Furans Tetrahydrofuran Cell Proliferation chemistry.chemical_classification Dose-Response Relationship Drug Diastereomer chemistry Molecular Medicine Enantiomer Drug Screening Assays Antitumor Lactone |
| Zdroj: | Journal of medicinal chemistry. 51(22) |
| ISSN: | 1520-4804 |
| Popis: | A systematic analysis using ten synthetic asimicin stereoisomers revealed that the stereochemistry of the bis-tetrahydrofuran core, including the tetrahydrofuran rings and the adjacent hydroxy functions, had significant effect on its cytotoxicity. Our findings set to rest the highly controversial perception that the stereochemistry of the tetrahydrofuran core has little effect on the activity, which is not true for its cytotoxic effect, and also reinforces the previous conclusion that asimicin is a highly potent anticancer compound. |
| Databáze: | OpenAIRE |
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