title: Synthesis of fluorinated brassinosteroids based on alkene cross-metathesis and preliminary biological assessment.
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.
authors.affiliation: Department of Organic and Nuclear Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, 128 43 Prague 2, Czech Republic.
authors.forename: Barbara
authors.initials: B
authors.lastname: Eignerová
authors.forename: Barbora
authors.initials: B
authors.lastname: Slavíková
authors.forename: Milos
authors.initials: M
authors.lastname: Budĕsínský
authors.forename: Martin
authors.initials: M
authors.lastname: Dracínský
authors.forename: Blanka
authors.initials: B
authors.lastname: Klepetárová
authors.forename: Eva
authors.initials: E
authors.lastname: St'astná
authors.forename: Martin
authors.initials: M
authors.lastname: Kotora
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D001681:Biological Assay; D060406:Brassinosteroids; D045744:Cell Line, Tumor; D002777:Cholestanols / Q000494:pharmacology; D055808:Drug Discovery; D054879:Halogenation; D006801:Humans; D008297:Male; D051381:Rats; D017208:Rats, Wistar; D011963:Receptors, GABA-A / Q000378:metabolism; D013256:Steroids / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D013260:Steroids, Heterocyclic / Q000494:pharmacology
chemical_list: D000475:Alkenes; D000970:Antineoplastic Agents; D060406:Brassinosteroids; D002777:Cholestanols; D011963:Receptors, GABA-A; D013256:Steroids; D013260:Steroids, Heterocyclic; C023623:brassinolide