Synthesis of fluorinated brassinosteroids based on alkene cross-metathesis and preliminary biological assessment.
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.
Eignerová
Barbara
B
Department of Organic and Nuclear Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, 128 43 Prague 2, Czech Republic.
Slavíková
Barbora
B
Budĕsínský
Milos
M
Dracínský
Martin
M
Klepetárová
Blanka
B
St'astná
Eva
E
Kotora
Martin
M
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
D000475:Alkenes; D000970:Antineoplastic Agents; D060406:Brassinosteroids; D002777:Cholestanols; D011963:Receptors, GABA-A; D013256:Steroids; D013260:Steroids, Heterocyclic; C023623:brassinolide