A Heck-Based Strategy To Generate Anacardic Acids and Related Phenolic Lipids for Isoform-Specific Bioactivity Profiling
| Autor: | David C. Martin, Amrik S. Kang, William K. Weigel, Taylor N. Dennis, J. Jefferson P. Perry |
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| Rok vydání: | 2018 |
| Předmět: |
Gene isoform
Alkenes Matrix Metalloproteinase Inhibitors 010402 general chemistry 01 natural sciences Biochemistry Structure-Activity Relationship chemistry.chemical_compound Phenols Heck reaction Organic chemistry Physical and Theoretical Chemistry Ginkgolic acid chemistry.chemical_classification Molecular Structure 010405 organic chemistry Alkene Organic Chemistry Stereoisomerism Lipids Salicylates Anacardic Acids 0104 chemical sciences Anacardic acids chemistry Stereoselectivity Oxidation-Reduction Palladium |
| Zdroj: | Organic Letters. 20:6234-6238 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.8b02705 |
| Popis: | A synthetic strategy for phenolic lipids such as anacardic acid and ginkgolic acid derivatives using an efficient and selective redox-relay Heck reaction followed by a stereoselective olefination is reported. This approach controls both the alkene position and stereochemistry, allowing the synthesis of natural and unnatural unsaturated lipids as single isomers. By this strategy, the activities of different anacardic acid and ginkgolic acid derivatives have been examined in a matrix metalloproteinase inhibition assay. |
| Databáze: | OpenAIRE |
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