Synthesis of fluorinated brassinosteroids based on alkene cross-metathesis and preliminary biological assessment
Language English Country United States Media print
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
19719120
DOI
10.1021/jm900495f
Knihovny.cz E-resources
- MeSH
- Alkenes chemistry MeSH
- Biological Assay MeSH
- Brassinosteroids MeSH
- Cholestanols pharmacology MeSH
- Halogenation * MeSH
- Rats MeSH
- Humans MeSH
- Cell Line, Tumor MeSH
- Drug Discovery MeSH
- Rats, Wistar MeSH
- Antineoplastic Agents chemical synthesis chemistry metabolism pharmacology MeSH
- Receptors, GABA-A metabolism MeSH
- Steroids, Heterocyclic pharmacology MeSH
- Steroids chemical synthesis chemistry metabolism pharmacology MeSH
- Animals MeSH
- Check Tag
- Rats MeSH
- Humans MeSH
- Male MeSH
- Animals MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Alkenes MeSH
- brassinolide MeSH Browser
- Brassinosteroids MeSH
- Cholestanols MeSH
- Antineoplastic Agents MeSH
- Receptors, GABA-A MeSH
- Steroids, Heterocyclic MeSH
- Steroids MeSH
Three types of brassinosteroid analogues with perfluoroalkylated side chains were synthesized by using alkene cross-metathesis of a brassinosteroid derivative bearing a terminal alkene moiety with different (perfluoroalkyl)propenes. The presence of the double bonds in the cross-metathesis products allowed a facile one-step double dihydroxylation to provide intermediates that after Baeyer-Villiger oxidation afforded the target compounds. Biological activity of the prepared analogues was tested in GABA(A) receptor, cytotoxic, and brassinolide activity, which reached in some cases the same range as their nonfluorinated analogues.
References provided by Crossref.org
Synthesis and Biological Activity of Brassinosteroid Analogues with a Nitrogen-Containing Side Chain
Computational study of productive and non-productive cycles in fluoroalkene metathesis
Cross-metathesis reaction of α- and β-vinyl C-glycosides with alkenes
Cross-metathesis of allylcarboranes with O-allylcyclodextrins
