Synthesis of fluorinated brassinosteroids based on alkene cross-metathesis and preliminary biological assessment
Jazyk angličtina Země Spojené státy americké Médium print
Typ dokumentu časopisecké články, práce podpořená grantem
PubMed
19719120
DOI
10.1021/jm900495f
Knihovny.cz E-zdroje
- MeSH
- alkeny chemie MeSH
- antitumorózní látky chemická syntéza chemie metabolismus farmakologie MeSH
- biotest MeSH
- brassinosteroidy MeSH
- cholestanoly farmakologie MeSH
- halogenace * MeSH
- krysa rodu Rattus MeSH
- lidé MeSH
- nádorové buněčné linie MeSH
- objevování léků MeSH
- potkani Wistar MeSH
- receptory GABA-A metabolismus MeSH
- steroidy heterocyklické farmakologie MeSH
- steroidy chemická syntéza chemie metabolismus farmakologie MeSH
- zvířata MeSH
- Check Tag
- krysa rodu Rattus MeSH
- lidé MeSH
- mužské pohlaví MeSH
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- alkeny MeSH
- antitumorózní látky MeSH
- brassinolide MeSH Prohlížeč
- brassinosteroidy MeSH
- cholestanoly MeSH
- receptory GABA-A MeSH
- steroidy heterocyklické MeSH
- steroidy 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.
Citace poskytuje Crossref.org
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