| Title | Synthesis of fluorinated brassinosteroids based on alkene cross-metathesis and preliminary biological assessment. | | Author(s) | Eignerová B, Slavíková B, Budĕsínský M, Dracínský M, Klepetárová B, St'astná E, Kotora M | | Institution | Department of Organic and Nuclear Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, 128 43 Prague 2, Czech Republic. | | Source | J Med Chem 2009 Sep 24; 52(18):5753-7. | | MeSH | Alkenes
Animals
Antineoplastic Agents
Biological Assay
Cell Line, Tumor
Cholestanols
Drug Discovery
Halogenation
Humans
Male
Rats
Rats, Wistar
Receptors, GABA-A
Steroids
Steroids, Heterocyclic
| | Abstract | 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. | | Language | eng | | Pub Type(s) | Journal Article
Research Support, Non-U.S. Gov't
| | PubMed ID | 19719120 |
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