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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.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Eignerová B,Slavíková B,Budĕsínský M,Dracínský M,Klepetárová B,St'astná E,Kotora M

doi

10.1021/jm900495f

subject

Has Abstract

pub_date

2009-09-24 00:00:00

pages

5753-7

issue

18

eissn

0022-2623

issn

1520-4804

journal_volume

52

pub_type

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